Information on EC 3.1.1.23 - acylglycerol lipase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY
3.1.1.23
-
RECOMMENDED NAME
GeneOntology No.
acylglycerol lipase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hydrolyses glycerol monoesters of long-chain fatty acids
show the reaction diagram
-
-
-
-
hydrolyses glycerol monoesters of long-chain fatty acids
show the reaction diagram
mechanism
-
hydrolyses glycerol monoesters of long-chain fatty acids
show the reaction diagram
the catalytic triad is composed of Ser110, Asp226 and His256 residues
-
hydrolyses glycerol monoesters of long-chain fatty acids
show the reaction diagram
the catalytic triad is composed of Ser110, Asp226 and His256 residues
-
-
hydrolyses glycerol monoesters of long-chain fatty acids
show the reaction diagram
mechanism
Pseudomonas sp. LP7315
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
esterification
-
-
hydrolysis
-
-
hydrolysis of carboxylic ester
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
monoacylglycerol metabolism (yeast)
-
-
triacylglycerol degradation
-
-
lipid metabolism
-
-
Glycerolipid metabolism
-
-
Metabolic pathways
-
-
SYSTEMATIC NAME
IUBMB Comments
glycerol-ester acylhydrolase
-
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
fatty acyl monoester lipase
-
-
-
-
glycerol-monoester acylhydrolase
-
-
lipase
Mortierella alliacea YN-15
-
-
-
lipozyme IM
-
-
MAG hydrolase
-
-
MAG lipase
-
-
MAGL
Rattus norvegicus Sprague-Dawley
-
-
-
MGL
Bacillus sp. H257
-
-
MGL
Mus musculus C57BL/6
-
-
-
MGL-like activity
-
MGLP
Bacillus subtilis H-257
-
-
-
monoacylglycerol hydrolase
-
-
-
-
monoacylglycerol hydrolase
-
-
monoacylglycerol lipase
-
-
-
-
monoacylglycerol lipase
-
monoacylglycerol lipase
Bacillus sp. H257
-
-
monoacylglycerol lipase
-
monoacylglycerol lipase
Mus musculus C57BL/6
-
;
-
monoacylglycerol lipase
-
-
monoacylglycerol lipase
Mycobacterium smegmatis mc2155
-
-
-
monoacylglycerol lipase
-
monoacylglycerol lipase
Rattus norvegicus Sprague-Dawley
-
-
-
monoglycerid lipase
-
-
monoglyceridase
-
-
-
-
monoglyceride hydrolase
-
-
-
-
monoglyceride lipase
-
-
-
-
monoglyceride lipase
-
-
monoglyceride lipase
-
monoglyceride lipase
-
-
monoglyceride lipase
-
-
monoglyceride lipase
-
-
-
monoglyceride lipase
-
-
monoglyceride lipase
-
-
monoglyceride lipase-like activity
-
monoglyceridyllipase
-
-
-
-
MSMEG_0220
-
gene name
MSMEG_0220
Mycobacterium smegmatis mc2155
-
gene name
-
Rv0183 protein
-
-
Rv0183 protein
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
9040-75-9
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
H-257
UniProt
Manually annotated by BRENDA team
strain H-257
-
-
Manually annotated by BRENDA team
strain H-257
-
-
Manually annotated by BRENDA team
Bacillus sp. H257
-
UniProt
Manually annotated by BRENDA team
strain H-257
-
-
Manually annotated by BRENDA team
Bacillus subtilis H-257
strain H-257
-
-
Manually annotated by BRENDA team
Mortierella alliacea YN-15
-
-
-
Manually annotated by BRENDA team
C57BL/6 mice
-
-
Manually annotated by BRENDA team
male albino Swiss-Webster mice
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57BL/6 mice
-
-
Manually annotated by BRENDA team
Mycobacterium smegmatis mc2155
-
-
-
Manually annotated by BRENDA team
strain H37Rv, gene Rv0183
-
-
Manually annotated by BRENDA team
strain H37Rv, gene Rv0183
-
-
Manually annotated by BRENDA team
strain LP7315
-
-
Manually annotated by BRENDA team
Pseudomonas sp. LP7315
strain LP7315
-
-
Manually annotated by BRENDA team
adult Sprague-Dawley rats
-
-
Manually annotated by BRENDA team
Sprague-Dawley rats
-
-
Manually annotated by BRENDA team
SpragueDawley rats
-
-
Manually annotated by BRENDA team
Wistar rats
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
Yju3p deficiency causes monoacylglycerol accumulation in vitro
malfunction
-
MGL inhibitors suppress formalin-induced pain through peripheral cannabinoid receptor 1 and cannabinoid receptor 2 receptor mechanisms. MGL inhibition increases paw skin 2-arachidonoylglycerol accumulation to mediate these effects
malfunction
-
disruption of MAGL expression and activity impairs cancer pathogenicity. impairments in MAGL-dependent tumor growth are rescued by a high-fat diet, indicating that exogenous sources of fatty acids can contribute to malignancy in cancers lacking MAGL activity
malfunction
-
MGL inactivation drives a CB1 cannabinoid receptor-dependent axonal growth response
malfunction
-
mice lacking MAGL exhibit dramatically reduced 2-arachidonoylglycerol hydrolase activity and highly elevated 2-arachidonoylglycerol levels in the nervous system leading to desensitization of brain CB1 receptors with a significant reduction of cannabimimetic effects of CB1 agonists. MAGL-deficient mice do not show alterations in neuropathic and inflammatory pain sensitivity
malfunction
-
enzyme inactivation attenuates hepatic ischemia/reperfusion-induced tissue injury, inflammation and oxidative stress
physiological function
-
key actor in endocannabinoid signaling
physiological function
-
Yju3p is required for efficient degradation of monoacylglycerol in yeast
physiological function
-
monoacylglycerol lipase (MAGL) regulates a fatty acid network that promotes cancer pathogenesis. MAGL, through hydrolysis of monoacylglycerols, controls free fatty acid levels in cancer cells
physiological function
-
monoacylglycerol lipase activity is a critical modulator of the tone and integrity of the endocannabinoid system
physiological function
-
monoacylglycerol lipase promotes hepatic injury via endocannabinoid and eicosanoid signaling
physiological function
-
over-expression of monoacylglycerol lipase in small intestine alters endocannabinoid levels and whole body energy balance, resulting in obesity
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1(3)-arachidonoylglycerol + H2O
? + glycerol
show the reaction diagram
-
-
-
?
1(3)-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
1(3)-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
1,3-dihydroxypropan-2-yl 4-pyren-1-ylbutanoate
pyrenylbutanoic acid + glycerol
show the reaction diagram
-
-
-
?
1,3-dihydroxypropan-2-yl 4-pyren-1-ylbutanoate + H2O
pyrenylbutanoic acid + glycerol
show the reaction diagram
-
-
-
?
1-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
1-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
1-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
best substrate
-
?
1-capryloyl-rac-glycerol + H2O
glycerol + caprylic acid
show the reaction diagram
-
-
-
?
1-decanoyl-rac-glycerol + H2O
glycerol + decanoic acid
show the reaction diagram
-
-
-
?
1-decanoyl-rac-glycerol + H2O
glycerol + decanoic acid
show the reaction diagram
-
best substrate
-
?
1-lauroyl-rac-glycerol + H2O
glycerol + lauric acid
show the reaction diagram
-
-
-
?
1-lauroyl-rac-glycerol + H2O
glycerol + lauric acid
show the reaction diagram
Bacillus sp., Bacillus sp. H257
-
more than 2fold higher activity compared to 1-oleoly-rac-glycerol
-
?
1-linoleoylglycerol + H2O
glycerol + linoleic acid
show the reaction diagram
-
-
-
?
1-mono-oleyl-rac-glycerol + H2O
oleate + glycerol
show the reaction diagram
-
-
-
?
1-monobutyroyl-rac-glycerol + H2O
butyrate + glycerol
show the reaction diagram
-
-
-
?
1-monocaprylin + H2O
?
show the reaction diagram
-
-
-
-
?
1-monocapryloylglycerol + H2O
caprylic acid + glycerol
show the reaction diagram
best substrate
-
?
1-monodecanoyl-rac-glycerol + H2O
decanoate + glycerol
show the reaction diagram
-
-
-
?
1-monolauroyl-rac-glycerol + H2O
laureate + glycerol
show the reaction diagram
-
-
-
?
1-monolauroylglycerol + H2O
lauric acid + glycerol
show the reaction diagram
-
best substrate
-
?
1-monolauroylglycerol + H2O
lauric acid + glycerol
show the reaction diagram
good substrate
-
?
1-monolauroylglycerol + H2O
lauric acid + glycerol
show the reaction diagram
-
best substrate
-
?
1-monolauroylglycerol + H2O
lauric acid + glycerol
show the reaction diagram
good substrate
-
?
1-monolinolein + H2O
?
show the reaction diagram
-
one of the most preferred substrates
-
-
?
1-monolinolenin + H2O
?
show the reaction diagram
-
best substrate
-
-
?
1-monolinoleoylglycerol + H2O
linolic acid + glycerol
show the reaction diagram
-
-
-
?
1-monolinoleoylycerol + H2O
linoleic acid + glycerol
show the reaction diagram
-
-
?
1-monomyristoyl-rac-glycerol + H2O
myristoate + glycerol
show the reaction diagram
-
-
-
?
1-monomyristoylglycerol + H2O
myristic acid + glycerol
show the reaction diagram
-
-
-
?
1-monomyristoylglycerol + H2O
myristic acid + glycerol
show the reaction diagram
-
best substrate
-
r
1-monomyristoylglycerol + H2O
myristic acid + glycerol
show the reaction diagram
good substrate
-
?
1-monomyristoylglycerol + H2O
myristic acid + glycerol
show the reaction diagram
Pseudomonas sp. LP7315
-
best substrate
-
r
1-monomyristoylglycerol + H2O
myristic acid + glycerol
show the reaction diagram
good substrate
-
?
1-monooctanoyl-rac-glycerol + H2O
octanoate + glycerol
show the reaction diagram
-
-
-
?
1-monoolein + H2O
?
show the reaction diagram
-
one of the most preferred substrates
-
-
?
1-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
1-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
1-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
1-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
?
1-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
Pseudomonas sp. LP7315
-
-
-
?
1-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
1-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
?
1-monopalmitin + H2O
?
show the reaction diagram
-
-
-
-
?
1-monopalmitoylglycerol + H2O
palmitic acid + glycerol
show the reaction diagram
-
-
-
?
1-monopalmitoylglycerol + H2O
palmitic acid + glycerol
show the reaction diagram
-
-
-
?
1-monopalmitoylglycerol + H2O
palmitic acid + glycerol
show the reaction diagram
-
-
-
r
1-monopalmitoylglycerol + H2O
palmitic acid + glycerol
show the reaction diagram
-
-
?
1-monopalmitoylglycerol + H2O
palmitic acid + glycerol
show the reaction diagram
Pseudomonas sp. LP7315
-
-
-
r
1-monopalmitoylglycerol + H2O
palmitic acid + glycerol
show the reaction diagram
-
-
?
1-monostearoylglycerol + H2O
stearic acid + glycerol
show the reaction diagram
-
-
?
1-myristoyl-rac-glycerol + H2O
glycerol + myristic acid
show the reaction diagram
-
-
-
?
1-oleoyl-rac-glycerol + H2O
glycerol + oleic acid
show the reaction diagram
Bacillus sp., Bacillus sp. H257
-
-
-
?
1-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
1-palmitoyl-2-lysophosphatidylcholine + H2O
palmitic acid + glycerophosphorylcholine
show the reaction diagram
-
-
-
?
2-(15-deoxy-DELTA12,14-prostaglandin J2)-glycerol + H2O
?
show the reaction diagram
-
-
-
-
?
2-(15-deoxy-DELTA12,14-prostaglandin J2)-glycerol + H2O
?
show the reaction diagram
-
highest preference
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
2-arachidonoylglycerol is an endocannabinoid which prevents the propagation of harmful neuroinflammation and may function as a gliotransmitter
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
the enzyme is responsible for degradation of 2-arachidonoylglycerol in HeLa cells
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
the enzyme is responsible for degradation of 2-arachidonoylglycerol in the brain
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
MGL modulates endocannabinoid signaling in vivo by inactivating 2-arachidonoylglycerol (2-AG), the main endogenous agonist for central CB1 and peripheral CB2 cannabinoid receptors
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
2-arachidonoylglycerol is bound in the tetrahedral intermediate state to Ser122
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
the MGL binding site is a single hydrophobic channel, consisting of an L-shaped main channel with a sub-pocket at the turn. The catalytic S122 of MGL is positioned at the bottom of a single channel
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
Rattus norvegicus Sprague-Dawley
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
presynaptic MGL not only hydrolyzes 2-arachidonoylglycerol released from activated postsynaptic neurons but also contributes to degradation of constitutively produced 2-arachidonoylglycerol and prevention of its accumulation around presynaptic terminals. Thus, the MGL activity determines basal endocannabinoid tone and terminates retrograde endocannabinoid signaling in the hippocampus
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
more than 80% of 2-arachidonoylglycerol (0.05 mM) is hydrolyzed after 90 min in the presence of 0.02 mg of MAGL(+/+) brain extracts at room temperature
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
Mus musculus C57BL/6
-
presynaptic MGL not only hydrolyzes 2-arachidonoylglycerol released from activated postsynaptic neurons but also contributes to degradation of constitutively produced 2-arachidonoylglycerol and prevention of its accumulation around presynaptic terminals. Thus, the MGL activity determines basal endocannabinoid tone and terminates retrograde endocannabinoid signaling in the hippocampus
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
Bacillus sp. H257
-
-
-
?
2-linoleoylglycerol + H2O
glycerol + linoleic acid
show the reaction diagram
-
-
-
?
2-monolinolein + H2O
?
show the reaction diagram
-
-
-
-
?
2-monomyristoylglycerol + H2O
myristic acid + glycerol
show the reaction diagram
-
-
-
?
2-monoolein + H2O
?
show the reaction diagram
-
-
-
-
-
2-monoolein + H2O
?
show the reaction diagram
-
-
-
-
-
2-monoolein + H2O
?
show the reaction diagram
-
-
-
-
?
2-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
r
2-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
r
2-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-monopalmitoylglycerol + H2O
palmitic acid + glycerol
show the reaction diagram
-
-
-
?
2-monopalmitoylglycerol + H2O
palmitic acid + glycerol
show the reaction diagram
-
-
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
Cys208 plays an important role in MGL function
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
Rattus norvegicus Sprague-Dawley
-
-
-
?
2-oleoylglycerol + H2O
glycerol + oleic acid
show the reaction diagram
-
-
-
?
2-palmitoylglycerol + H2O
glycerol + palmitic acid
show the reaction diagram
-
-
-
?
3-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
4-methylumbelliferyl butyrate + H2O
4-methylumbelliferol + butyrate
show the reaction diagram
-
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
?
4-nitrophenyl butyrate + H2O
4-nitrophenol + butyric acid
show the reaction diagram
-
-
?
4-nitrophenyl caprate + H2O
4-nitrophenol + capric acid
show the reaction diagram
-
-
?
4-nitrophenyl caprylate + H2O
4-nitrophenol + caprylic acid
show the reaction diagram
-
-
?
4-nitrophenyl octanoate + H2O
4-nitrophenol + octanoate
show the reaction diagram
-
-
?
4-nitrophenyl-caproate + H2O
4-nitrophenol + caproic acid
show the reaction diagram
-
-
?
4-nitrophenyl-laurate + H2O
4-nitrophenol + lauric acid
show the reaction diagram
-
-
?
4-nitrophenyl-myristate + H2O
4-nitrophenol + myristic acid
show the reaction diagram
-
-
?
4-nitrophenyl-palmitate + H2O
4-nitrophenol + palmitic acid
show the reaction diagram
-
-
?
4-nitrophenyl-stearate + H2O
4-nitrophenol + stearic acid
show the reaction diagram
-
-
?
4-nitrophenyllaurate + H2O
4-nitrophenol + lauric acid
show the reaction diagram
-
-
-
?
4-nitrophenyllaurate + H2O
4-nitrophenol + lauric acid
show the reaction diagram
Pseudomonas sp., Pseudomonas sp. LP7315
-
-
-
r
4-nitrophenyllaurate + H2O
4-nitrophenol + lauric acid
show the reaction diagram
Pseudomonas sp. LP7315
-
-
-
?
7-hydroxycoumarinyl arachidonate
arachidonic acid + 7-hydroxycoumarin
show the reaction diagram
-
-
-
?
arachidonoyl-1-thio-glycerol + H2O
?
show the reaction diagram
Bacillus sp., Bacillus sp. H257
-
-
-
-
?
arachidonoyl-7-hydroxy-6-methoxy-4-methylcoumarin ester + H2O
arachidonic acid + 7-hydroxy-6-methoxy-4-methylcoumarin
show the reaction diagram
-
-
-
?
arachidonoyl-7-hydroxy-6-methoxy-4-methylcoumarin ester + H2O
arachidonic acid + 7-hydroxy-6-methoxy-4-methylcoumarin
show the reaction diagram
-
-
-
?
arachidonoyl-7-hydroxy-6-methoxy-4-methylcoumarin ester + H2O
arachidonic acid + 7-hydroxy-6-methoxy-4-methylcoumarin
show the reaction diagram
-
-
?
bis(monoacylclycerol) phosphate + H2O
?
show the reaction diagram
-
at pH 5.5
-
-
?
glycerol + lauric acid
monolaurin + H2O
show the reaction diagram
-
93% conversion after 6 h
-
r
glycerol + myristic acid
monomyristin + H2O
show the reaction diagram
-
60% conversion after 6 h
-
r
glycerol + oleic acid
monoolein + H2O
show the reaction diagram
-
46% conversion after 6 h
-
r
glycerol + palmitic acid
monopalmitin + H2O
show the reaction diagram
-
50% conversion after 6 h
-
r
glycerol + stearic acid
monostearin + H2O
show the reaction diagram
-
60% conversion after 6 h
-
r
lauric acid + glycerol
monolauroyl glycerol + H2O
show the reaction diagram
-
catalyzes the esterification of lauric acid and glycerol in a homogeneous system, minimal amounts of dilaurin are also synthesized
-
?
lysobisphosphatidic acid + H2O
?
show the reaction diagram
-
at pH 5.5
-
-
?
methyl butyrate + H2O
methanol + butanoate
show the reaction diagram
-
-
-
?
methylcaprylate + H2O
?
show the reaction diagram
-
low activity
-
-
?
methyloleate + H2O
?
show the reaction diagram
-
low activity
-
-
?
monoarachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
monolinoleoylglycerol + H2O
linoic acid + glycerol
show the reaction diagram
-
-
-
?
monolinoleoylglycerol + H2O
linoic acid + glycerol
show the reaction diagram
-
-
-
?
monomyristin + H2O
glycerol + myristate
show the reaction diagram
Mycobacterium smegmatis, Mycobacterium smegmatis mc2155
-
-
-
?
monomyristoylglycerol + H2O
myristic acid + glycerol
show the reaction diagram
-
-
-
?
monoolein + H2O
glycerol + oleate
show the reaction diagram
Mycobacterium smegmatis, Mycobacterium smegmatis mc2155
-
-
-
?
monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
monooleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
preferred substrate
-
?
monostearoylglycerol + H2O
stearic acid + glycerol
show the reaction diagram
-
-
-
?
oleoylethanol + H2O
oleic acid + ethanol
show the reaction diagram
-
-
-
?
palmitoyl-CoA + H2O
palmitic acid + CoA
show the reaction diagram
-
-
-
?
phosphatidylcholine + H2O
?
show the reaction diagram
Mortierella alliacea, Mortierella alliacea YN-15
-
one of the most preferred substrates
-
-
?
prostaglandin D2-G + H2O
?
show the reaction diagram
-
-
-
-
?
prostaglandin D2-glycerol + H2O
?
show the reaction diagram
-
-
-
-
?
prostaglandin E2-G + H2O
?
show the reaction diagram
-
-
-
-
?
prostaglandin E2-glycerol + H2O
?
show the reaction diagram
-
-
-
-
?
prostaglandin F2alpha-glycerol + H2O
?
show the reaction diagram
-
-
-
-
?
prostaglandin F3alpha-G + H2O
?
show the reaction diagram
-
-
-
-
?
rac-1(3)-oleoylglycerol + H2O
oleate + glycerol
show the reaction diagram
-
-
-
?
sn-2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
sn-2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
sn-2-monoolein + H2O
glycerol + oleic acid
show the reaction diagram
Mus musculus, Homo sapiens, Mus musculus C57BL/6
-
-
-
?
sn-2-palmitoylglycerol + H2O
palmitic acid + glycerol
show the reaction diagram
-
-
-
?
tributyrylglycerol + H2O
?
show the reaction diagram
-
-
-
-
?
tricaprylin + H2O
?
show the reaction diagram
Mortierella alliacea, Mortierella alliacea YN-15
-
-
-
-
?
trieicosapentaenoin + H2O
?
show the reaction diagram
-
low activity
-
-
?
trilaurin + H2O
?
show the reaction diagram
-
low activity
-
-
?
trilinolein + H2O
?
show the reaction diagram
-
low activity
-
-
?
trilinolenin + H2O
?
show the reaction diagram
-
low activity
-
-
?
triolein + H2O
?
show the reaction diagram
Mortierella alliacea, Mortierella alliacea YN-15
-
the lipase strongly hydrolyzes the sn-1/3 ester bonds and weakly hydrolyzes the sn-2 ester bonds of triolein
-
-
?
tripalmitin + H2O
?
show the reaction diagram
-
-
-
-
?
tripalmitolein + H2O
?
show the reaction diagram
-
-
-
-
?
tristearin + H2O
?
show the reaction diagram
-
-
-
-
?
umbelliferyl arachidonate + H2O
umbelliferol + arachidonic acid
show the reaction diagram
-
-
-
?
monostearoylglycerol + H2O
stearic acid + glycerol
show the reaction diagram
-
-
-
?
additional information
?
-
-
-
-
-
-
additional information
?
-
-
no activity against long-chain diacylglycerols and triacylglycerols, cholesterol ester, or lysophosphatidylcholine
-
-
-
additional information
?
-
-
enzyme also catalyzes monoglyceride synthesis in a solvent-free two-phase system, in which fatty acid droplets are dispersed in the glycerol phase with a low water content, enzyme does not hydrolyze di- and triglycerides
-
-
?
additional information
?
-
enzyme does not hydrolyze palmitoylethanolamine, enzyme preferentially hydrolyzes 2-monoglycerides
-
-
?
additional information
?
-
-
enzyme exhibits both phosphatidic acid-preferring phospholipase A2 and monoacylglycerol lipase activities with a modest specificity towards unsaturated acyl chains, veryl low di- and triaclyglycerol lipase activity
-
-
?
additional information
?
-
-
hydrolyzes monoacylglycerols but not di- or triacylglycerols
-
-
?
additional information
?
-
preferentially hydrolyzes triacylglycerol-esters and 4-nitrophenyl-esters of fatty acids with short chain lengths up to 10 carbon atoms, no hydrolysis of triolein
-
-
?
additional information
?
-
-
catalyzes the last step in the hydrolysis of stored triglycerides in the adipocytes
-
-
-
additional information
?
-
-
monoacylglycerol lipase is required in the final hydrolysis of 2-monoacylglycerols produced by hormone-sensitive lipase
-
-
-
additional information
?
-
-
inhibition of the enzyme potentiates the activation of 2-arachidonoylglycerol production by ATP
-
-
-
additional information
?
-
-
enzyme activity with 1-, 2-, and 3- monoacylglycerols as substrates is similar, enzyme activity with 1-, 2-, and 3-monoacylglycerols as substrates is similar
-
-
-
additional information
?
-
-
developmental and nutritional regulation of the enzyme in the intestine, overview
-
-
-
additional information
?
-
-
key enzyme responsible for the termination of endocannabinoid signaling with a crucial role in 2-arachidonoylglycerol metabolism, MAGL is unable to mediate anandamide degradation, overview
-
-
-
additional information
?
-
-
Rv0183, as exported enzyme, may be involved in the degradation of the host cell lipids
-
-
-
additional information
?
-
-
the enzyme is involved in prostaglandin metabolism in brain particulate fractions
-
-
-
additional information
?
-
-
tissue-specific developmental and nutritional regulation of the enzyme, post-transcriptional regulation of expression occurs in the intestine, while transcriptional regulation is the primary mechanism for hepatic MGL expression, overview
-
-
-
additional information
?
-
-
substate specificity, overview
-
-
-
additional information
?
-
-
substrate specificity, the enzyme hydrolyses monoacylglycerol substrates, both long chain di- and triacylglycerols, although the turnover is lower than with monoacylglycerol, overview, no activity of the recombinant enzyme with lysophospholipid substrates, recombinant Rv0183 hydrolyses synthetic vinyl esters with various acyl chain lengths, chain length dependence, overview
-
-
-
additional information
?
-
-
monoacylglycerols containing long-chain unsaturated fatty acids and phosphatidylcholine are preferentially hydrolyzed over triacylglycerols and fatty acid methyl esters. Triacylglycerol may be formed via 2-monoacylglycerol
-
-
-
additional information
?
-
-
no activity with triacetin, tributyrin, trioctanoin, triolein, dioctanoin, dimyristin, monooctanoin, diolein, and Tween 80
-
-
-
additional information
?
-
-
the enzyme also uses soybean oil, sesame oil, rapeseed oil, camellia oil, olive oil and linseed oil as substrates. 1,3-dicaprylin, 1,3-dipalmitin, 1,2-diolein, 1,3-diolein, 1,2-dilinolein, methylbutyrate, methyllaurate, methylpalmitate, methylpamitoleate, methylsterate, methyllinoleate, methyllinolenate, and methyleicosapentaenoate yield no detectable activity at either 30 or 50C
-
-
-
additional information
?
-
Mycobacterium smegmatis mc2155
-
no activity with triacetin, tributyrin, trioctanoin, triolein, dioctanoin, dimyristin, monooctanoin, diolein, and Tween 80
-
-
-
additional information
?
-
Bacillus subtilis H-257
-
hydrolyzes monoacylglycerols but not di- or triacylglycerols
-
-
?
additional information
?
-
Pseudomonas sp. LP7315
-
enzyme also catalyzes monoglyceride synthesis in a solvent-free two-phase system, in which fatty acid droplets are dispersed in the glycerol phase with a low water content, enzyme does not hydrolyze di- and triglycerides
-
-
?
additional information
?
-
Mus musculus C57BL/6
-
tissue-specific developmental and nutritional regulation of the enzyme, post-transcriptional regulation of expression occurs in the intestine, while transcriptional regulation is the primary mechanism for hepatic MGL expression, overview
-
-
-
additional information
?
-
-
Rv0183, as exported enzyme, may be involved in the degradation of the host cell lipids, substrate specificity, the enzyme hydrolyses monoacylglycerol substrates, both long chain di- and triacylglycerols, although the turnover is lower than with monoacylglycerol, overview, no activity of the recombinant enzyme with lysophospholipid substrates, recombinant Rv0183 hydrolyses synthetic vinyl esters with various acyl chain lengths, chain length dependence, overview
-
-
-
additional information
?
-
Mortierella alliacea YN-15
-
monoacylglycerols containing long-chain unsaturated fatty acids and phosphatidylcholine are preferentially hydrolyzed over triacylglycerols and fatty acid methyl esters. Triacylglycerol may be formed via 2-monoacylglycerol, the enzyme also uses soybean oil, sesame oil, rapeseed oil, camellia oil, olive oil and linseed oil as substrates. 1,3-dicaprylin, 1,3-dipalmitin, 1,2-diolein, 1,3-diolein, 1,2-dilinolein, methylbutyrate, methyllaurate, methylpalmitate, methylpamitoleate, methylsterate, methyllinoleate, methyllinolenate, and methyleicosapentaenoate yield no detectable activity at either 30 or 50C
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
1-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
best substrate
-
?
1-lauroyl-rac-glycerol + H2O
glycerol + lauric acid
show the reaction diagram
Bacillus sp., Bacillus sp. H257
-
more than 2fold higher activity compared to 1-oleoly-rac-glycerol
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
2-arachidonoylglycerol is an endocannabinoid which prevents the propagation of harmful neuroinflammation and may function as a gliotransmitter
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
the enzyme is responsible for degradation of 2-arachidonoylglycerol in HeLa cells
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
-
the enzyme is responsible for degradation of 2-arachidonoylglycerol in the brain
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
Q99685
MGL modulates endocannabinoid signaling in vivo by inactivating 2-arachidonoylglycerol (2-AG), the main endogenous agonist for central CB1 and peripheral CB2 cannabinoid receptors
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
-
presynaptic MGL not only hydrolyzes 2-arachidonoylglycerol released from activated postsynaptic neurons but also contributes to degradation of constitutively produced 2-arachidonoylglycerol and prevention of its accumulation around presynaptic terminals. Thus, the MGL activity determines basal endocannabinoid tone and terminates retrograde endocannabinoid signaling in the hippocampus
-
?
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
show the reaction diagram
Rattus norvegicus Sprague-Dawley
-
-
-
?
2-arachidonoylglycerol + H2O
glycerol + arachidonic acid
show the reaction diagram
Mus musculus C57BL/6
-
presynaptic MGL not only hydrolyzes 2-arachidonoylglycerol released from activated postsynaptic neurons but also contributes to degradation of constitutively produced 2-arachidonoylglycerol and prevention of its accumulation around presynaptic terminals. Thus, the MGL activity determines basal endocannabinoid tone and terminates retrograde endocannabinoid signaling in the hippocampus
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
-
-
-
?
2-oleoylglycerol + H2O
oleic acid + glycerol
show the reaction diagram
Rattus norvegicus, Rattus norvegicus Sprague-Dawley
-
-
-
?
arachidonoyl-7-hydroxy-6-methoxy-4-methylcoumarin ester + H2O
arachidonic acid + 7-hydroxy-6-methoxy-4-methylcoumarin
show the reaction diagram
Q99685
-
-
?
additional information
?
-
-
-
-
-
-
additional information
?
-
-
catalyzes the last step in the hydrolysis of stored triglycerides in the adipocytes
-
-
-
additional information
?
-
-
monoacylglycerol lipase is required in the final hydrolysis of 2-monoacylglycerols produced by hormone-sensitive lipase
-
-
-
additional information
?
-
-
inhibition of the enzyme potentiates the activation of 2-arachidonoylglycerol production by ATP
-
-
-
additional information
?
-
-
developmental and nutritional regulation of the enzyme in the intestine, overview
-
-
-
additional information
?
-
-
key enzyme responsible for the termination of endocannabinoid signaling with a crucial role in 2-arachidonoylglycerol metabolism, MAGL is unable to mediate anandamide degradation, overview
-
-
-
additional information
?
-
-
Rv0183, as exported enzyme, may be involved in the degradation of the host cell lipids
-
-
-
additional information
?
-
-
the enzyme is involved in prostaglandin metabolism in brain particulate fractions
-
-
-
additional information
?
-
Mus musculus, Mus musculus C57BL/6
-
tissue-specific developmental and nutritional regulation of the enzyme, post-transcriptional regulation of expression occurs in the intestine, while transcriptional regulation is the primary mechanism for hepatic MGL expression, overview
-
-
-
additional information
?
-
-
Rv0183, as exported enzyme, may be involved in the degradation of the host cell lipids
-
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
-
slightly activating
Na+
-
110% activity at 1 mM
Ca2+
-
129% activity at 1 mM
additional information
-
not activated by K+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(2R,9Z)-octadec-9-ene-1,2-diamine dihydrochloride
-
inhibits by 42.2%
(2S)-6-[4-(hexyloxy)phenyl]hexane-1,2-diamine
-
exhibits weak inhibitory activity (25.9%)
(2S,9Z)-octadec-9-ene-1,2-diamine
-
selectively inhibits MGL by 49.9%. The presence of a long monounsaturated chain corresponding to oleic acid is a key requirement for the selective inhibition of MGL
(3R)-1-(3,4-dimethylphenyl)-5-oxo-N-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]pyrrolidine-3-carboxamide
-
51.85% residual activity at 0.1 mM
(3R)-N-(3,5-dimethylphenyl)-1-[2-(5-fluoro-1H-indol-3-yl)ethyl]-5-oxopyrrolidine-3-carboxamide
-
18.61% residual activity at 0.1 mM
(3S)-3-[1(R)-(biphenylacetyloxy)-ethyl]-azetidin-2-one
-
16% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
(3S)-N-(1,3-benzodioxol-4-ylmethyl)-1-[4-[(2-chlorobenzyl)oxy]phenyl]-5-oxopyrrolidine-3-carboxamide
-
51.09% residual activity at 0.1 mM
(4-amidinophenyl) methanesulfonyl fluoride
-
i.e. APMSF, inhibits at 0.5 mM
(5E)-5-(3-methylbutylidene)-2-thioxo-1,3-thiazolidin-4-one
-
weak inhibitory effect
(5Z,8Z,11Z,14Z)-eicosantetraenoic acid 3-thienyl methyl ester
-
i.e. CAY-10402, 14% inhibition at 0.1 mM
(R)-2-aminohexadecanol
-
inhibits by 30%
(S)-2-aminohexadecanol
-
inhibits by 31.5%
1,2-diaminohexadecane
-
inhibits by 30.3%
1-(20-cyano-16,16-dimethyl-eicosa-5,8,11,14-tetraenoyl)glycerol
-
i.e. O-223
1-(20-hydroxy-16,16-dimethyl-eicosa-5,8,11,14-tetraenoyl)glycerol
-
i.e. O-224
1-(3-phenylpropanoyl)-(3R,4R)-3-[1(R)-(3-phenylpropanoyloxy)-ethyl]-4-(acetoxy)-azetidin-2-one
-
100% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(3-phenylpropanoyl)-(3R,4R)-3-[1(R)-(4-phenylbutanoyloxy)-ethyl]-4-(acetoxy)-azetidin-2-one
-
100% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(3-phenylpropanoyl)-(3R,4R)-3-[1(R)-(biphenylacetyloxy)-ethyl]-4-(acetoxy)-azetidin-2-one
-
100% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0; 66% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(3-phenylpropanoyl)-(3S)-3-[1(R)-(3-phenylpropanoyloxy)-ethyl]-azetidin-2-one
-
100% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(3-phenylpropanoyl)-(3S)-3-[1(R)-(4-phenylbutanoyloxy)-ethyl]-azetidin-2-one
-
100% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(3-phenylpropanoyl)-(3S)-3-[1(R)-(5-phenylpentanoyloxy)-ethyl]-azetidin-2-one
-
100% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(3-phenylpropanoyl)-(3S)-3-[1(R)-(biphenylacetyloxy)-ethyl]-azetidin-2-one
-
31% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(4-phenylbutanoyl)-(3R,4R)-3-[1(R)-(4-phenylbutanoyloxy)-ethyl]-4-(acetoxy)-azetidin-2-one
-
100% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(4-phenylbutanoyl)-(3R,4R)-3-[1(R)-hydroxyethyl]-4-(acetoxy)-azetidin-2-one
-
61% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(4-phenylbutanoyl)-(3S)-3-[1(R)-(3-phenylpropanoyloxy)-ethyl]-azetidin-2-one
-
54% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(4-phenylbutanoyl)-(3S)-3-[1(R)-(4-phenylbutanoyloxy)-ethyl]-azetidin-2-one
-
100% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(4-phenylbutanoyl)-(3S)-3-[1(R)-(5-phenylpentanoyloxy)-ethyl]-azetidin-2-one
-
59% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(5-phenylpentanoyl)-(3S)-3-[1(R)-(4-phenylbutanoyloxy)-ethyl]-azetidin-2-one
-
39% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(5-phenylpentanoyl)-(3S)-3-[1(R)-(biphenylacetyloxy)-ethyl]-azetidin-2-one
-
25% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(hexa-5-enoyl)-(3S)-3-[1(R)-(4-phenylbutanoyloxy)-ethyl]-azetidin-2-one
-
85% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(hexa-5-enoyl)-(3S)-3-[1(R)-(biphenylacetyloxy)-ethyl]-azetidin-2-one
-
67% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(pent-4-enoyl)-(3R,4R)-3-[1(R)-(pent-4-enoyloxy)-ethyl]-4-(acetoxy)-azetidin-2-one
-
99% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(pent-4-enoyl)-(3R,4R)-3-[1(R)-hydroxyethyl]-4-(acetoxy)-azetidin-2-one
-
16% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0; 8% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(pent-4-enoyl)-(3S)-3-[1(R)-(4-phenylbutanoyloxy)-ethyl]-azetidin-2-one
-
89% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(pent-4-enoyl)-(3S)-3-[1(R)-(biphenylacetyloxy)-ethyl]-azetidin-2-one
-
91% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(pent-4-enoyl)-(3S)-3-[1(R)-(hexa-5-enoyloxy)-ethyl]-azetidin-2-one
-
8% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(pent-4-enoyl)-(3S)-3-[1(R)-(pent-4-enoyloxy)-ethyl]-azetidin-2-one
-
99% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-(pent-4-enoyl)-(3S)-3-[1(R)-hydroxyethyl]-azetidin-2-one
-
89% inhibition, with 0.1 mM of inhibitor, at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
1-arachidin
-
11% inhibition of the membraneous enzyme at 0.1 mM, 19% inhibition of the cytosolic enzyme at 0.1 mM
1-arachidonoylglycerol
-
IC50 value for the membraneous enzyme is 0.0095 mM, for the cytosolic enzyme 0.0071 mM, complete inhibition is possible
1-arachidonoylglycerol
-
inhibits the hydrolysis of cytosolic 2-oleoylglycerol, IC50 value is 0.017 mM, the affinity for the enzyme is highest with an arachidonyl side chain and decreases to fatty acids of shorter chain length
1-methylethyl dodecylphosphonofluoridoate
-
highly potent inhibitor
1-myristin
-
IC50 value for the membraneous and the cytosolic enzyme is 0.032 mM, complete inhibition is possible
1-nor-arachidonoyl-3-(2'3-dihydroxypropyl) urea
-
i.e. O-1502, 39% inhibition at 0.1 mM
1-palmitin
-
44% inhibition of the membraneous enzyme at 0.1 mM, 38% inhibition of the cytosolic enzyme at 0.1 mM
15-deoxy-DELTA12,14-prostaglandin J2
-
-
1H-benzotriazol-1-yl(4-benzylpiperazin-1-yl)methanone
-
-
1H-benzotriazol-1-yl[4-(4-bromobenzyl)piperazin-1-yl]methanone
-
-
1H-benzotriazol-1-yl[4-(4-nitrobenzyl)piperazin-1-yl]methanone
-
-
1H-benzotriazol-1-yl[4-(naphthalen-2-ylmethyl)piperazin-1-yl]methanone
-
-
1H-benzotriazol-1-yl[4-[(2E)-3-phenylprop-2-en-1-yl]piperazin-1-yl]methanone
-
-
2,3-dihydroxypropyl (11Z)-icos-11-enoate
-
i.e. O-4066, IC50 value for the membraneous enzyme is 0.026 mM, for the cytosolic enzyme 0.019 mM, complete inhibition of the membraneous enzyme is possible, maximal inhibition of the cytosolic enzyme of 79%
2,3-dihydroxypropyl (11Z,14Z)-icosa-11,14-dienoate
-
i.e. O-3907, IC50 value for the membraneous enzyme is 0.016 mM, for the cytosolic enzyme 0.0051 mM, complete inhibition is possible
2,3-dihydroxypropyl (4Z,7Z,10Z,13Z)-17-ethylcycloheptadeca-4,7,10,13-tetraene-1-carboxylate
-
i.e. O-1428, IC50 value for the membraneous enzyme is 0.071 mM, for the cytosolic enzyme 0.015 mM, complete inhibition is possible
2,3-dihydroxypropyl (5Z)-icos-5-enoate
-
i.e. 3908, IC50 value for the membraneous enzyme is 0.056 mM, for the cytosolic enzyme 0.021 mM, complete inhibition of the membraneous enzyme is possible, maximal inhibition of the cytosolic enzyme of 65%
2,3-dihydroxypropyl (5Z,8Z,11Z)-2-ethylcycloheptadeca-5,8,11-triene-1-carboxylate
-
i.e. O-3973, IC50 value for the membraneous enzyme is 0.0083 mM, for the cytosolic enzyme 0.0042 mM, complete inhibition is possible
2,3-dihydroxypropyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
-
i.e. O-3832, IC50 value for the membraneous enzyme is 0.017 mM, for the cytosolic enzyme 0.0082 mM, complete inhibition is possible
2,3-dihydroxypropyl (6Z,9Z,12Z,15Z)-cyclohenicosa-6,9,12,15-tetraene-1-carboxylate
-
IC50 value for the membraneous enzyme is 0.0051 mM, for the cytosolic enzyme 0.0058 mM, complete inhibition is possible
2,3-dihydroxypropyl (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoate
-
IC50 value for the membraneous enzyme is 0.011 mM, for the cytosolic enzyme 0.0045 mM, complete inhibition is possible
2,3-dihydroxypropyl (8Z,11Z,14Z)-icosa-8,11,14-trienoate
-
i.e. 3846, IC50 value for the membraneous enzyme is 0.073 mM, for the cytosolic enzyme 0.0075 mM, complete inhibition is possible
2-(7-methoxy-2-oxo-2H-chromen-3-yl)-N-(2-methoxyphenyl)-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxamide
-
-
2-(nonylsulfanyl)-4H-1,3,2-benzodioxaphosphinine 2-oxide
-
-
2-arachidonoylglycerol
-
inhibits the hydrolysis of cytosolic 2-oleoylglycerol, IC50 value is 0.013 mM, the affinity for the enzyme is highest with an arachidonyl side chain and decreases to fatty acids of shorter chain length
2-arachidonoylglycerol
-
-
2-mercaptoethanol
-
50% residual activity at 1 mM
2-methyl-4-isothiazolin-3-one
-
-
2-octyl-4-isothiazolin-3-one
-
; octhilinone, inhibits purified recombinant MGL through a partially reversible mechanism that involves a specific interaction with cysteine 208
2-octyl-benzo[d]isothiazol-3-one
-
-
2-oleoyl-4-isothiazolin-3-one
-
-
3-methoxy-N-phenyl-1,2,4-thiadiazol-5-amine
-
weak inhibitory effect
3-[(4S)-1-[2-(5-fluoro-1H-indol-3-yl)ethyl]-2,5-dioxoimidazolidin-4-yl]-N-[(1R,2R)-2-methylcyclohexyl]propanamide
-
57.6% residual activity at 0.1 mM
4-chlormercurybenzoate
-
IC50 value is 0.072 mM
4-chloromercuribenzoic acid
-
-
4-cyanophenyl ethyl dodecylphosphonate
-
highly potent inhibitor
4-nitrophenyl 4-[bis(1,3-benzodioxol-5-yl)hydroxymethyl]piperidine-1-carboxylate
-
JZL184
4-nitrophenyl dodecyl(1-methylethyl)phosphinate
-
-
5-[(biphenyl-4-yl)methyl]-N,N-dimethyl-2H-tetrazole-2-carboxamide
-
AM6701, conforms to the L shape of the binding site, contacts with the binding site are similar to those seen with the 2-arachidonoylglycerol docking pose. The close contacts with A164 and K165 are lost as the subpocket is not occupied. Instead the biphenyl moiety, which extends further up the binding pocket, makes additional contacts with A156, T157 and K160, thus AM6701 is a non-selective inhibitor
6-methyl-2-p-tolylamino-benzo[d] [1,3]oxazin-4-one
-
i.e. URB754
6-methyl-2-p-tolylamino-benzo[d] [1,3]oxazin-4-one
-
i.e. URB754
6-methyl-2-[(4-methylphenyl)amino]-4H-3,1-benzoxazin-4-one
-
URB754, inhibition of brain MAGL expressed in HeLa cells, no inhibition of membrane-bound MAGL. Is not selective for MAGL
alpha-methyl-1-arachidonoyl glycerol
-
compound O-1428, inhibits both cytosolic and membrane-bound MAGL
alpha-methyl-1-arachidonoylglycerol
-
IC50 value is 0.011 mM
AM6580
-
irreversible inhibitor, i.e. [4-(9H-fluoren-9-yl)-piperazin-1-yl][1,2,3]triazolo[4,5-b]pyridin-1-ylmethanone
-
AM6701
-
5-((biphenyl-4-yl)methyl)-N,N-dimethyl-2H-tetrazole-2-carboxamide
AM6701
-
MGL inhibition by AM6701 involves a covalent interaction resulting in the enzyme's rapid, selective carbamoylation at its catalytic serine nucleophile (Ser122)
AM6701
-
slowly reversible inhibition, i.e. 5-((biphenyl-4-yl)methyl)-N,N-dimethyl-2H-tetra-zole-2-carboxamide
AM6702
-
-
apolipoprotein A-1
-
-
-
arachidonic acid
-
IC50 value is 0.078 mM
arachidonoyl glycine
-
42% inhibition at 0.1 mM
arachidonoyl serinol
-
IC50 value is 0.073 mM
arachidonoyl trifluoromethylketone
-
50% inhibition at 0.066 mM
arachidonoyl trifluoromethylketone
-
50% inhibition at 0.0025 mM
arachidonoyl trifluoromethylketone
-
the affinity for the enzyme is highest with an arachidonyl side chain and decreases to fatty acids of shorter chain length
arachidonoyl trifluoromethylketone
-
causes a gradual suppression of cannabinoid-sensitive IPSCs in cultured hippocampal neurons, the suppression is reversed by blocking CB1 receptors and is attenuated by inhibiting 2-AG synthesis, overview
arachidonoyltrifluoromethyl ketone
-
i.e. ATFMK
arachidonoyltrifluoromethyl ketone
-
i.e. ATFMK, inhibition is reversible by AM281
arachidonoyltrifluoromethylketone
-
-
arachidonyl trifluoromethylketone
-
-
ATP
-
slightly inhibiting
benzol
-
IC50 is 0.012 mM
benzyl [4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-2-methylphenyl]carbamate
-
5.12% residual activity at 0.1 mM
benzylphenylcarbamate
-
-
biphenyl-3-yl-carbamic acid cyclohexyl ester
-
i.e. URB602
CAY10499
-
-
celastrol
-
inhibits MGL activity, albeit less potently than pristimerin
chlorpyrifos oxon
-
IC50 is 34 nM
chlorpyrifos oxon
-
is not selective for MAGL
Co2+
-
47% residual activity at 1 mM
Cu2+
-
35% residual activity at 1 mM
decyl benzodioxaphosphorin oxide
-
IC50 is 0.80 nM
deoxycholate
-
17% inhibition at 5 mM
diazoxon
-
IC50 is 0.014 mM
dichlorvos
-
IC50 is 0.013 mM
diethyl 3,5,6-trichloropyridin-2-yl phosphate
-
-
diethyl 4-nitrophenyl phosphate
-
-
Diethyl p-nitrophenyl phosphate
-
-
Diethyl p-nitrophenyl phosphate
-
-
diethyldicarbonate
-
20% residual activity at 1 mM
dihydrocelastrol
-
inhibits MGL activity, albeit less potently than pristimerin
dihydrocelastryl diacetate
-
inhibits MGL activity, albeit less potently than pristimerin
diisopropyl fluorophosphate
-
i.e. DFP, n-C8H17P(O)(OCH3)F, IC50 is 0.045 mM
diisopropyl fluorophosphate
-
-
diisopropyl fluorophosphate
-
-
diisopropylfluorophosphate
-
75% residual activity at 1 mM
Disulfiram
-
i.e. tetraethylthiuram disulfide, a compound used to treat alcoholism, inhibition likely through an interaction with cysteine residues Cys208 and/or Cys242, the inhibition is reversible by DTT
Disulfiram
-
-
dithiothreitol
-
-
dodecane-1-sulfonyl fluoride
-
-
dodecyl benzodioxaphosphorin oxide
-
IC50 is 0.83 nM
dodecyl sulfonyl fluoride
-
IC50 is 200 nM
E600
-
inactivation
EDTA
-
50% residual activity at 1 mM
ethyl 3,5,6-trichloropyridin-2-yl dodecylphosphonate
-
-
ethyl octylphosphonofluoridate
-
i.e. EOFP, n-C8H17P(O)(OC2H5)F, IC50 is 3.0 nM
ethyl octylphosphonofluoridate
-
is not selective for MAGL
euphol
-
inhibits MGL activity with high potency. Blocks MGL activity through a reversible and noncompetitive mechanism, which is apparently identical to that of pristimerin
Fe3+
-
35% residual activity at 1 mM
heptyl benzodioxaphosphorin oxide
-
IC50 is 45 nM
hexadecylsufonyl fluoride
-
50% inhibition at 0.000241 mM
hexadecylsufonyl fluoride
-
50% inhibition at 0.0062 mM
Hg2+
-
30% residual activity at 1 mM
HgCl2
-
IC50 value is 0.042 mM
HgCl2
-
HgCl2
isopropyl dodecylfluorophosphate
-
i.e. IDFP, n-C12H25P(O)(OCH3)F, IC50 is 0.76 nM
isopropyl dodecylfluorophosphonate
-
is not selective for MAGL
isopropyldodecylfluorophosphonate
-
-
JJKK-048
-
i.e. 4-[bis-(benzo[d][1,3]dioxol-5-yl)methyl]-piperidin-1-yl}(1H-1,2,4-triazol-1-yl)methanone
-
JZL184
-
is more potent than LY2183240. The p-nitrophenyl group fits better in the MAGL cavity than the corresponding substituent of LY2183240
JZL184
-
MGL-selective inhibitor, represents a ligand with increased steric bulk over AM6701 and 2-arachidonoylglycerol. Extra bulk fills the binding site more completely and one 1,3-benzodioxole moiety makes additional contacts with the lid region of MGL. There is also a weak hydrogen bond from N195 to the p-nitro substituent
JZL184
-
time-dependent inhibitor
JZL184
-
irreversible inhibitor
JZL184
-
irreversible inhibitor
JZL184
-
-
JZL184
-
selective inhibitor
JZL184
-
i.e. 4-nitrophenyl 4-(dibenzo[d][1,3]dioxol-5-yl(hydroxy)methyl)piperidine-1-carboxylate
LY2183240
-
is less potent than JZL184
Maleimide
-
IC50 value is 0.070 mM
Mercury chloride
-
-
methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14- tetraenylphosphonofluoridate
-
completely inhibits 4-nitophenyl acetate hydrolysis by pure human MGL at 0.1 mM
methyl arachidonyl fluorophosphonate
-
50% inhibition at 0.0000022 mM
methyl arachidonyl fluorophosphonate
-
i.e. MAFP, inhibits at 0.05 mM
methyl arachidonyl fluorophosphonate
-
50% inhibition at 0.0008 mM
methyl arachidonyl fluorophosphonate
-
-
methyl arachidonyl fluorophosphonate
-
i.e. MAFP, n-C20H33P(O)(OCH3)F
methyl arachidonyl fluorophosphonate
-
i.e. MAFP
methyl arachidonyl fluorophosphonate
-
causes a gradual suppression of cannabinoid-sensitive IPSCs in cultured hippocampal neurons, the suppression is reversed by blocking CB1 receptors and is attenuated by inhibiting 2-AG synthesis, overview; i.e. MAFP
methyl arachidonyl fluorophosphonate
-
MAFP
methyl arachidonyl fluorophosphonate
-
irreversible active-site inhibitor of monoglyceride lipase
methyl icosylphosphonofluoridoate
-
-
methyl octylphosphonofluoridate
-
i.e. MOFP, n-C8H17P(O)(OCH3)F, IC50 is 3.0 nM
methyl octylphosphonofluoridate
-
is not selective for MAGL
methylarachidonoylfluorophosphonate
-
-
-
N-(1-pyrenyl)-maleimide
-
IC50 value is 0.068 mM
N-(2-hydroxyethyl)-2-oxopentadecanamide
-
exhibits weak inhibitory activity (27.5%) and no selectivity towards MGL
N-(4-hydroxy-2-methylphenyl)arachidonylamide
-
i.e. VDM11, an anandamide uptake inhibitor, substrate of fatty acid amide hydrolase, EC 3.5.1.4, IC50 is 0.021 mM
N-(4-hydroxyphenyl)arachidonylamide
-
i.e. AM404, an anandamide uptake inhibitor, substrate of fatty acid amide hydrolase, EC 3.5.1.4, IC50 is 0.020 mM
N-arachidonoyl dopamine
-
-
N-arachidonoyl dopamine
-
-
N-arachidonoylmaleimide
-
IC50 value is 0.00014 mM
N-arachidonoylmaleimide
-
irreversible inhibition
N-arachidonoylmaleimide
-
inhibits MGL through partial enzyme alkylation at Cys208 and/or Cys242 (Cys242 being favored)
N-arachidonoylmaleimide
-
-
N-arachidonyl maleimide
-
protects 2-arachidonoylglycerol from metabolic degradation
N-arachidonyl maleimide
-
potent irreversible inhibitor of MAGL, inhibits in a dose-dependent manner
N-arachidonylmaleimide
-
-
N-arachidonylmaleimide
-
; inhibitory effect is attributed to the ability of this compound to react with C242 and form a Michael addition product
N-arachidonylmaleimide
-
Cys201 is the crucial residue in MAGL inhibition by N-arachidonylmaleimide
N-arachidonylmaleimide
-
inhibits membrane-bound MAGL selectively
N-benzoylthiocarbamic cyclohexylethyl ester
-
-
N-cyclohexylmaleimide
-
IC50 value is 0.051 mM
N-ethylmaleimide
-
-
N-ethylmaleimide
-
-
N-hydroxymaleimide
-
IC50 value is 0.413 mM
N-n-heptyl benzodioxaphosphorin oxide
-
IC50 is 150 nM
N-Phenylmaleimide
-
IC50 value is 0.044 mM
N-propylmaleimide
-
IC50 value is 0.053 mM
N-[3-(4-fluorophenyl)-6-oxopyrazolo[5,1-c]pyrido[4,3-e][1,2,4]triazin-7(6H)-yl]-2-(naphthalen-2-yloxy)acetamide
-
72.3% residual activity at 0.1 mM
N-[4-(1,3-benzothiazol-2-yl)phenyl]-2-(1H-benzotriazol-1-yl)acetamide
-
14.28% residual activity at 0.1 mM
NaCl
-
1 M, 63% loss of activity
NEM
-
IC50 value is 0.053 mM
noladin ether
-
IC50 value is 0.036 mM
O-n-octyl benzodioxaphosphorin oxide
-
IC50 is 150 nM
octane-1-sulfonyl fluoride
-
-
octyl sulfonyl fluoride
-
IC50 is 140 nM
p-bromophenacyl bromide
-
partial inhibition
p-chloromercuribenzoic acid
-
45% residual activity at 1 mM
palmitoyl-CoA
-
-
Paraoxon
-
IC50 is 0.0023 mM
phenylmethylsulfonyl fluoride
-
50% inhibition at 0.155 mM
phenylmethylsulfonyl fluoride
-
inhibits MGL only at very high concentrations
phenylmethylsulfonyl fluoride
-
70% residual activity at 1 mM
phenylmethylsulfonyl fluoride
-
-
PMSF
-
inactivation
PMSF
-
-
pristimerin
-
inhibits MGL activity with high potency. Addition to purified MGL produces an almost immediate blockade of MGL activity. Inhibits MGL through a mechanism that is rapid, reversible, and noncompetitive
pristimerin
-
-
pristimerol
-
inhibits MGL activity, albeit less potently than pristimerin
Protamine sulfate
-
-
-
S-heptyl benzodioxaphosphorin oxide
-
IC50 is 2.9 nM
S-nonyl benzodioxaphosphorin oxide
-
IC50 is 0.31 nM
S-nonylbenzodioxaphosphorin oxide
-
is not selective for MAGL
S-pentyl benzodioxaphosphorin oxide
-
IC50 is 3.1 nM
SAR629
-
substrate mimic
Sodium cholate
-
-
SPB 01403
-
-
stearyl benzodioxaphosphorin oxide
-
IC50 is 51 nM
tetrahydrolipstatin
-
inactivation
tetrahydrolipstatin
-
-
tetrahydrolipstatin
-
-
Triton X-100
-
10% inhibition at 0.25%
troglitazone
-
-
troglitazone
-
-
URB-602
-
a specific MGL inhibitor
URB602
-
specific inhibitor of MAGL, inhibits in a dose-dependent manner
URB602
-
reversible inhibitor
URB602
-
-
Zn2+
-
27% residual activity at 1 mM
[1,1'-biphenyl]-3-yl-carbamic acid, cyclohexyl ester
-
URB602, noncompetetive selective inhibitor
[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]carbamic acid benzyl ester
-
CAY10499
[4-[bis(1,3-benzodioxol-5-yl)methyl]-1-piperidinyl](1H-1,2,4-triazol-1-yl)methanone
-
a highly potent selective inhibitor
Mn2+
-
58% residual activity at 1 mM
additional information
-
inhibitory potency of different 1-arachidonic acid analogues, the chain length of the fatty acid is important for affinity and inhibition, while methylations of the fatty acids do not influence the inhibitory potency, overview
-
additional information
-
no inhibition by URB597, bovine serum albumin decreases the inhibitory effect of arachidonoyl-based compounds, e.g. VDM11
-
additional information
-
inhibition by bulky maleimides derivatives is due to steric hindrance of substrate binding after alkylation of cysteines 242 and/or 208, no inhibition by succimide and N-arachidonylsuccimide
-
additional information
-
no inhibition by PMSF and palmityl trifluoromethyl ketone
-
additional information
-
immunodepletion of the enzyme leads to 50% reduced activity
-
additional information
-
immunodepletion of the recombinant enzyme leads to 50% reduced activity
-
additional information
-
analysis of structure-function relationships; analysis of structure-function relationships, organophosphorus-induced in vivo inhibition, overview
-
additional information
-
inactivation by serine esterase inhibitors
-
additional information
-
no inhibition by URB754
-
additional information
-
inhibitor screening, molecular docking and modeling, no inhibition of MGL by fatty acid amide hydrolase inhibitors, overview
-
additional information
-
inhibitor screening, overview
-
additional information
-
inhibitors of other endocannabinoid hydrolyzing enzymes, fatty acid amide hydrolase and cyclooxygenase-2, have no effect on the 2-AG-induced IPSC suppression
-
additional information
-
not inhibited by CAY10433, WWL70, and URB602
-
additional information
-
URB754 does not inhibit MAGL activity at concentrations up to 0.100 mM. Assay buffer alone or heat-denatured MAGL protein has no significant activity against 7-hydroxycoumarinyl-arachidonate
-
additional information
-
(2S)-6-phenylhexane-1,2-diamine and (2S,9Z)-2-aminooctadec-9-enamide show no inhibition
-
additional information
-
3-methoxy-N-phenyl-1,2,4-thiadiazol-5-amine and 3-propoxy-2-benzofuran-1(3H)-one do not inhibit
-
additional information
-
is not inhibited by 1 mM N-arachidonylsuccinimide
-
additional information
-
1-(4-phenylbutanoyl)-(3S)-3-[1(R)-hydroxyethyl]-azetidin-2-one, 1-(5-phenylpentanoyl)-(3S)-3-[1(R)-hydroxyethyl]-azetidin-2-one, 1-(hexa-5-enoyl)-(3S)-3-[1(R)-hydroxyethyl]-azetidin-2-one and 1-(4-phenylbutanoyl)-(3S)-3-[1(R)-(biphenylacetyloxy)-ethyl]-azetidin-2-one do not inhibit
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
bovine serum albumin
-
MAGL activity increases with increasing concentration up to 1%
-
EDTA
-
slightly activating
EDTA
-
activates
EGTA
-
activates
ethanol
-
activates 1.5fold at 5% v/v
NMDA
-
stimulates activity
taurodeoxycholate
-
dependent on, maximal activity at 1-5 mM
glutamate
-
stimulates activity
additional information
-
high fat feeding induces the enzyme in the intestine, but starvation does not have an effect on the enzyme activity
-
additional information
-
dimethyl sulfoxide concentrations up to 10% of the final assay volume have no effect on MAGL activity, the inclusion of dimethyl sulfoxide in the assay can increase the solubility of hydrophobic compounds
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.02
1-decanoyl-rac-glycerol
-
at pH 7.4 and 37C
0.14
1-monolauroylglycerol
-
pH 7.3, 37C
0.12
1-monomyristoylglycerol
-
-
0.083
1-monooleoylglycerol
-
pH 7.3, 37C
0.3
1-monooleoylglycerol
-
pH 7, 22C
0.51
1-monooleoylglycerol
-
-
0.01
2-(15-deoxy-DELTA12,14-prostaglandin J2)-glycerol
-
mutant enzyme C242A, at pH 7.4 and 37C
-
0.0122
2-(15-deoxy-DELTA12,14-prostaglandin J2)-glycerol
-
at pH 7.4 and 37C
-
0.013
2-(15-deoxy-DELTA12,14-prostaglandin J2)-glycerol
-
mutant enzyme C201A, at pH 7.4 and 37C
-
0.015
2-(15-deoxy-DELTA12,14-prostaglandin J2)-glycerol
-
wild type enzyme, at pH 7.4 and 37C
-
0.016
2-(15-deoxy-DELTA12,14-prostaglandin J2)-glycerol
-
mutant enzyme C208A, at pH 7.4 and 37C
-
0.0097
2-arachidonoylglycerol
-
at pH 7.4 and 37C
0.01
2-arachidonoylglycerol
-
pH 8.0, 37C
0.0197
2-arachidonoylglycerol
-
recombinant enzyme, in TME buffer, at 37C
0.0336
2-arachidonoylglycerol
-
native enzyme, in TME buffer, at 37C
0.044
2-arachidonoylglycerol
-
pH and temperature not specified in the publication
0.2
2-monomyristoylglycerol
-
-
0.059
2-monooleoylglycerol
-
pH 7.3, 37C
0.000014
2-oleoylglycerol
-
in the presence of 0.0005 mM pristimerin, at pH 7.5, 37C
0.000024
2-oleoylglycerol
-
in the presence of 0.0003 mM pristimerin, at pH 7.5, 37C
0.000027
2-oleoylglycerol
-
in the presence of 0.0001 mM pristimerin, at pH 7.5, 37C
0.000028
2-oleoylglycerol
-
in the presence of vehicle (0.1% DMSO), at pH 7.5, 37C
0.0022
2-oleoylglycerol
-
pH 7.2, 37C, cytosolic fraction
0.098
2-oleoylglycerol
-
mutant C242G
0.115
2-oleoylglycerol
-
wild-type
0.084
4-Methylumbelliferyl butyrate
-
mutant enzyme L167Q/L171Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C; mutant enzyme L167Q/L174Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.089
4-Methylumbelliferyl butyrate
-
mutant enzyme L171Q/L174Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.09
4-Methylumbelliferyl butyrate
-
mutant enzyme L169S/L176S/K160A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.105
4-Methylumbelliferyl butyrate
-
mutant enzyme L171Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.11
4-Methylumbelliferyl butyrate
-
mutant enzyme L169S/L176S/K226A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.123
4-Methylumbelliferyl butyrate
-
mutant enzyme L169S/L176S/K36A/K226A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.124
4-Methylumbelliferyl butyrate
-
mutant enzyme L169S/L176S/K36A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.136
4-Methylumbelliferyl butyrate
-
mutant enzyme L169S/L176S, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.137
4-Methylumbelliferyl butyrate
-
mutant enzyme L169S/L176S/K165A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.162
4-Methylumbelliferyl butyrate
-
wild type enzyme, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.2
4-nitrophenylacetate
-
-
0.0098
7-hydroxycoumarinyl arachidonate
-
at pH 8 and 25C, in 10% dimethyl sulfoxide
1.25
arachidonoyl-1-thio-glycerol
-
in 10 mM Tris-HCl (pH 7.2), temperature not specified in the publication
-
0.0088
arachidonoyl-7-hydroxy-6-methoxy-4-methylcoumarin ester
-
recombinant enzyme, in TME buffer, at 37C
0.47
oleoylethanol
-
-
-
0.133
prostaglandin D2-G
-
pH 8.0, 37C
0.15
prostaglandin E2-G
-
pH 8.0, 37C
0.311
prostaglandin F3alpha-G
-
pH 8.0, 37C
0.27
sn-1(3)-monooleoylglycerol
-
-
-
0.49
sn-2-monooleoylglycerol
-
-
0.49
sn-2-monooleoylglycerol
-
-
40
Tributyrylglycerol
-
-
200
methyl butyrate
-
-
additional information
additional information
-
kinetics
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.35
2-arachidonoylglycerol
Rattus norvegicus
-
pH 8.0, 37C
0.45
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L169S/L176S/K165A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.5
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L169S/L176S/K160A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C; mutant enzyme L169S/L176S/K36A/K226A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.63
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L169S/L176S/K226A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.78
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L171Q/L174Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.8
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L169S/L176S, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.85
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L169S/L176S/K36A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C; mutant enzyme L171Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
0.98
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L167Q/L171Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
1.13
4-Methylumbelliferyl butyrate
Homo sapiens
-
wild type enzyme, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
1.17
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L167Q/L174Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
2.66
arachidonoyl-1-thio-glycerol
Bacillus sp.
-
in 10 mM Tris-HCl (pH 7.2), temperature not specified in the publication
-
0.07
prostaglandin D2-G
Rattus norvegicus
-
pH 8.0, 37C
0.16
prostaglandin E2-G
Rattus norvegicus
-
pH 8.0, 37C
0.14
prostaglandin F3alpha-G
Rattus norvegicus
-
pH 8.0, 37C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3.3
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L169S/L176S/K165A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
2465
4.2
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L169S/L176S/K36A/K226A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
2465
5.5
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L169S/L176S/K160A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
2465
5.8
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L169S/L176S, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C; mutant enzyme L169S/L176S/K226A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
2465
6.8
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L169S/L176S/K36A, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
2465
7
4-Methylumbelliferyl butyrate
Homo sapiens
-
wild type enzyme, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
2465
8
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L171Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
2465
8.7
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L171Q/L174Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
2465
11.8
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L167Q/L171Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
2465
13.8
4-Methylumbelliferyl butyrate
Homo sapiens
-
mutant enzyme L167Q/L174Q, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
2465
2.1
arachidonoyl-1-thio-glycerol
Bacillus sp.
-
in 10 mM Tris-HCl (pH 7.2), temperature not specified in the publication
197670
1.5
umbelliferyl arachidonate
Homo sapiens
-
wild type enzyme, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
166173
1.7
umbelliferyl arachidonate
Homo sapiens
-
mutant enzyme L169S/L176S, in 20 mM PIPES, pH 7.0, and 150 mM NaCl at 37C
166173
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.039
(2R,9Z)-octadec-9-ene-1,2-diamine dihydrochloride
-
-
0.0218
(2S,9Z)-octadec-9-ene-1,2-diamine
-
-
0.0587
1,2-diaminohexadecane
-
-
additional information
additional information
-
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.1
(3R)-1-(3,4-dimethylphenyl)-5-oxo-N-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]pyrrolidine-3-carboxamide
Homo sapiens
-
IC50 around 0.1 mM, pH and temperature not specified in the publication
0.000039
(3R)-N-(3,5-dimethylphenyl)-1-[2-(5-fluoro-1H-indol-3-yl)ethyl]-5-oxopyrrolidine-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.1
(3S)-N-(1,3-benzodioxol-4-ylmethyl)-1-[4-[(2-chlorobenzyl)oxy]phenyl]-5-oxopyrrolidine-3-carboxamide
Homo sapiens
-
IC50 around 0.1 mM, pH and temperature not specified in the publication
0.02
(5E)-5-(3-methylbutylidene)-2-thioxo-1,3-thiazolidin-4-one
Rattus norvegicus
-
recombinant purified enzyme, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/ml bovine serum albumin, fatty acid-free
0.00851
1-(hexa-5-enoyl)-(3S)-3-[1(R)-(4-phenylbutanoyloxy)-ethyl]-azetidin-2-one
Homo sapiens
-
at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
0.0146
1-(hexa-5-enoyl)-(3S)-3-[1(R)-(biphenylacetyloxy)-ethyl]-azetidin-2-one
Homo sapiens
-
at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
0.133
1-(pent-4-enoyl)-(3R,4R)-3-[1(R)-(pent-4-enoyloxy)-ethyl]-4-(acetoxy)-azetidin-2-one
Homo sapiens
-
at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
0.00406
1-(pent-4-enoyl)-(3S)-3-[1(R)-(4-phenylbutanoyloxy)-ethyl]-azetidin-2-one
Homo sapiens
-
at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
0.00184
1-(pent-4-enoyl)-(3S)-3-[1(R)-(biphenylacetyloxy)-ethyl]-azetidin-2-one
Homo sapiens
-
at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
0.00472
1-(pent-4-enoyl)-(3S)-3-[1(R)-(hexa-5-enoyloxy)-ethyl]-azetidin-2-one
Homo sapiens
-
at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
0.0233
1-(pent-4-enoyl)-(3S)-3-[1(R)-(pent-4-enoyloxy)-ethyl]-azetidin-2-one
Homo sapiens
-
at 37C for 10 min, in 10 mM Tris-HCl buffer, 1 mM EDTA, 0.1% (w/v) bovine serum albumin, pH 8.0
0.0095
1-arachidonoylglycerol
Rattus norvegicus
-
IC50 value for the membraneous enzyme is 0.0095 mM, for the cytosolic enzyme 0.0071 mM, complete inhibition is possible
0.017
1-arachidonoylglycerol
Rattus norvegicus
-
inhibits the hydrolysis of cytosolic 2-oleoylglycerol, IC50 value is 0.017 mM, the affinity for the enzyme is highest with an arachidonyl side chain and decreases to fatty acids of shorter chain length
0.0000008
1-methylethyl dodecylphosphonofluoridoate
Mus musculus
-
-
0.032
1-myristin
Rattus norvegicus
-
IC50 value for the membraneous and the cytosolic enzyme is 0.032 mM, complete inhibition is possible
0.026
2,3-dihydroxypropyl (11Z)-icos-11-enoate
Rattus norvegicus
-
i.e. O-4066, IC50 value for the membraneous enzyme is 0.026 mM, for the cytosolic enzyme 0.019 mM, complete inhibition of the membraneous enzyme is possible, maximal inhibition of the cytosolic enzyme of 79%
0.016
2,3-dihydroxypropyl (11Z,14Z)-icosa-11,14-dienoate
Rattus norvegicus
-
i.e. O-3907, IC50 value for the membraneous enzyme is 0.016 mM, for the cytosolic enzyme 0.0051 mM, complete inhibition is possible
0.071
2,3-dihydroxypropyl (4Z,7Z,10Z,13Z)-17-ethylcycloheptadeca-4,7,10,13-tetraene-1-carboxylate
Rattus norvegicus
-
i.e. O-1428, IC50 value for the membraneous enzyme is 0.071 mM, for the cytosolic enzyme 0.015 mM, complete inhibition is possible
0.056
2,3-dihydroxypropyl (5Z)-icos-5-enoate
Rattus norvegicus
-
i.e. 3908, IC50 value for the membraneous enzyme is 0.056 mM, for the cytosolic enzyme 0.021 mM, complete inhibition of the membraneous enzyme is possible, maximal inhibition of the cytosolic enzyme of 65%
0.0083
2,3-dihydroxypropyl (5Z,8Z,11Z)-2-ethylcycloheptadeca-5,8,11-triene-1-carboxylate
Rattus norvegicus
-
i.e. O-3973, IC50 value for the membraneous enzyme is 0.0083 mM, for the cytosolic enzyme 0.0042 mM, complete inhibition is possible
0.017
2,3-dihydroxypropyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
Rattus norvegicus
-
i.e. O-3832, IC50 value for the membraneous enzyme is 0.017 mM, for the cytosolic enzyme 0.0082 mM, complete inhibition is possible
0.0051
2,3-dihydroxypropyl (6Z,9Z,12Z,15Z)-cyclohenicosa-6,9,12,15-tetraene-1-carboxylate
Rattus norvegicus
-
IC50 value for the membraneous enzyme is 0.0051 mM, for the cytosolic enzyme 0.0058 mM, complete inhibition is possible
0.011
2,3-dihydroxypropyl (7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoate
Rattus norvegicus
-
IC50 value for the membraneous enzyme is 0.011 mM, for the cytosolic enzyme 0.0045 mM, complete inhibition is possible
0.073
2,3-dihydroxypropyl (8Z,11Z,14Z)-icosa-8,11,14-trienoate
Rattus norvegicus
-
i.e. 3846, IC50 value for the membraneous enzyme is 0.073 mM, for the cytosolic enzyme 0.0075 mM, complete inhibition is possible
0.00000031
2-(nonylsulfanyl)-4H-1,3,2-benzodioxaphosphinine 2-oxide
Mus musculus
-
-
0.013
2-arachidonoylglycerol
Rattus norvegicus
-
inhibits the hydrolysis of cytosolic 2-oleoylglycerol, IC50 value is 0.013 mM, the affinity for the enzyme is highest with an arachidonyl side chain and decreases to fatty acids of shorter chain length
1
2-mercaptoethanol
Mortierella alliacea
-
in 50 mM phosphate buffer (pH 7.4), at 30C
0.000239
2-methyl-4-isothiazolin-3-one
Rattus norvegicus
-
recombinant purified enzyme, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/ml bovine serum albumin, fatty acid-free
0.000151
2-octyl-4-isothiazolin-3-one
Rattus norvegicus
-
wild-type, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/ml bovine serum albumin, fatty acid-free
0.000722
2-octyl-4-isothiazolin-3-one
Rattus norvegicus
-
mutant C208G, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/ml bovine serum albumin, fatty acid-free
0.000059
2-octyl-benzo[d]isothiazol-3-one
Rattus norvegicus
-
recombinant purified enzyme, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/ml bovine serum albumin, fatty acid-free
0.000043
2-oleoyl-4-isothiazolin-3-one
Rattus norvegicus
-
recombinant purified enzyme, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/ml bovine serum albumin, fatty acid-free
0.028
3-methoxy-N-phenyl-1,2,4-thiadiazol-5-amine
Rattus norvegicus
-
recombinant purified enzyme, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/ml bovine serum albumin, fatty acid-free
0.1
3-[(4S)-1-[2-(5-fluoro-1H-indol-3-yl)ethyl]-2,5-dioxoimidazolidin-4-yl]-N-[(1R,2R)-2-methylcyclohexyl]propanamide
Homo sapiens
-
IC50 above 0.1 mM, pH and temperature not specified in the publication
0.072
4-chlormercurybenzoate
Rattus norvegicus
-
IC50 value is 0.072 mM
0.00000007
4-cyanophenyl ethyl dodecylphosphonate
Mus musculus
-
-
0.00021
4-nitrophenyl 4-[bis(1,3-benzodioxol-5-yl)hydroxymethyl]piperidine-1-carboxylate
Homo sapiens
-
at 37C, pH 7.0, incubation time of 15 min, without Triton X-100
0.0017
4-nitrophenyl 4-[bis(1,3-benzodioxol-5-yl)hydroxymethyl]piperidine-1-carboxylate
Homo sapiens
-
at 37C, pH 7.0, incubation time of 15 min, in the presence of 0.2% (m/v) Triton X-100
0.0037
4-nitrophenyl 4-[bis(1,3-benzodioxol-5-yl)hydroxymethyl]piperidine-1-carboxylate
Homo sapiens
-
at 37C, pH 7.0, incubation time of 15 min, in the presence of 0.2% (m/v) Triton X-100
0.00000028
4-nitrophenyl dodecyl(1-methylethyl)phosphinate
Mus musculus
-
-
0.0002
6-methyl-2-[(4-methylphenyl)amino]-4H-3,1-benzoxazin-4-one
Rattus norvegicus
-
MAGL expressed in HeLa cells
0.01
alpha-methyl-1-arachidonoyl glycerol
Rattus norvegicus
-
cytosolic MAGL
0.015
alpha-methyl-1-arachidonoyl glycerol
Rattus norvegicus
-
cytosolic MAGL
0.071
alpha-methyl-1-arachidonoyl glycerol
Rattus norvegicus
-
membrane-bound MAGL
0.011
alpha-methyl-1-arachidonoylglycerol
Rattus norvegicus
-
IC50 value is 0.011 mM
0.0031
AM404
Homo sapiens
-
pH and temperature not specified in the publication
0.0000009
AM6701
Homo sapiens
-
native enzyme, in 50 mM Tris-HCl (pH 7.4) containing 8% DMSO, at room temperature
0.0000017
AM6701
Homo sapiens
-
recombinant enzyme, in 50 mM Tris-HCl (pH 7.4) containing 8% DMSO, at room temperature
0.0001
AM6702
Homo sapiens
-
native enzyme, in 50 mM Tris-HCl (pH 7.4) containing 8% DMSO, at room temperature
0.0028
AM6702
Homo sapiens
-
native enzyme, in 50 mM Tris-HCl (pH 7.4) containing 8% DMSO, at room temperature
0.078
arachidonic acid
Rattus norvegicus
-
IC50 value is 0.078 mM
0.073
arachidonoyl serinol
Rattus norvegicus
-
IC50 value is 0.073 mM
0.00184
arachidonoyltrifluoromethylketone
Homo sapiens
-
-
0.012
benzol
Mus musculus
-
IC50 is 0.012 mM
0.000424
benzyl [4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-2-methylphenyl]carbamate
Homo sapiens
-
pH and temperature not specified in the publication
0.0004
CAY10499
Homo sapiens
-
using 2-oleoylglycerol as a substrate
0.0005
CAY10499
Homo sapiens
-
using 4-nitophenyl acetate as a substrate
0.0016
celastrol
Rattus norvegicus
-
purified MGL, at pH 7.5, 37C
0.000034
chlorpyrifos oxon
Mus musculus
-
IC50 is 34 nM
0.000034
chlorpyrifos oxon
Rattus norvegicus
-
cytosolic MAGL
0.0049
CP55,940
Homo sapiens
-
pH and temperature not specified in the publication
0.0000008
decyl benzodioxaphosphorin oxide
Mus musculus
-
IC50 is 0.80 nM
0.014
diazoxon
Mus musculus
-
IC50 is 0.014 mM
0.013
dichlorvos
Mus musculus
-
IC50 is 0.013 mM
0.00001
diethyl 3,5,6-trichloropyridin-2-yl phosphate
Mus musculus
-
-
0.0023
diethyl 4-nitrophenyl phosphate
Mus musculus
-
-
0.015
dihydrocelastrol
Rattus norvegicus
-
purified MGL, at pH 7.5, 37C
0.015
dihydrocelastryl diacetate
Rattus norvegicus
-
purified MGL, at pH 7.5, 37C
0.045
diisopropyl fluorophosphate
Mus musculus
-
i.e. DFP, n-C8H17P(O)(OCH3)F, IC50 is 0.045 mM
0.0008
Disulfiram
Homo sapiens
-
-
0.0002
dodecane-1-sulfonyl fluoride
Mus musculus
-
-
0.00000083
dodecyl benzodioxaphosphorin oxide
Mus musculus
-
IC50 is 0.83 nM
0.0002
dodecyl sulfonyl fluoride
Mus musculus
-
IC50 is 200 nM
1
EDTA
Mortierella alliacea
-
in 50 mM phosphate buffer (pH 7.4), at 30C
0.00000014
ethyl 3,5,6-trichloropyridin-2-yl dodecylphosphonate
Mus musculus
-
-
0.000003
ethyl octylphosphonofluoridate
Mus musculus
-
i.e. EOFP, n-C8H17P(O)(OC2H5)F, IC50 is 3.0 nM
0.000003
ethyl octylphosphonofluoridate
Rattus norvegicus
-
cytosolic MAGL
0.000315
euphol
Rattus norvegicus
-
purified MG, at pH 7.5, 37CL
0.000882
euphol
Rattus norvegicus
-
nonpurified MGL, at pH 7.5, 37C
0.000045
heptyl benzodioxaphosphorin oxide
Mus musculus
-
IC50 is 45 nM
0.042
HgCl2
Rattus norvegicus
-
IC50 value is 0.042 mM
0.00000076
isopropyl dodecylfluorophosphate
Mus musculus
-
i.e. IDFP, n-C12H25P(O)(OCH3)F, IC50 is 0.76 nM
0.00000076
isopropyl dodecylfluorophosphonate
Rattus norvegicus
-
cytosolic MAGL
0.07
Maleimide
Rattus norvegicus
-
IC50 value is 0.070 mM
0.000076
methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-ylphosphonofluoridate
Homo sapiens
-
-
0.000033
methyl arachidonyl fluorophosphonate
Homo sapiens
-
at 37C, pH 7.0, incubation time of 15 min, without Triton X-100
0.000062
methyl arachidonyl fluorophosphonate
Homo sapiens
-
at 37C, pH 7.0, incubation time of 15 min, in the presence of 0.2% (m/v) Triton X-100
0.00016
methyl arachidonyl fluorophosphonate
Homo sapiens
-
at 37C, pH 7.0, incubation time of 15 min, in the presence of 0.2% (m/v) Triton X-100
0.000002
methyl icosylphosphonofluoridoate
Mus musculus
-
-
0.000003
methyl octylphosphonofluoridate
Mus musculus
-
i.e. MOFP, n-C8H17P(O)(OCH3)F, IC50 is 3.0 nM
0.068
N-(1-pyrenyl)-maleimide
Rattus norvegicus
-
IC50 value is 0.068 mM
0.021
N-(4-hydroxy-2-methylphenyl)arachidonylamide
Rattus norvegicus
-
i.e. VDM11, an anandamide uptake inhibitor, substrate of fatty acid amide hydrolase, EC 3.5.1.4, IC50 is 0.021 mM
0.02
N-(4-hydroxyphenyl)arachidonylamide
Rattus norvegicus
-
i.e. AM404, an anandamide uptake inhibitor, substrate of fatty acid amide hydrolase, EC 3.5.1.4, IC50 is 0.020 mM
0.00078
N-arachidonoyl dopamine
Homo sapiens
-
pH and temperature not specified in the publication
0.00014
N-arachidonoylmaleimide
Rattus norvegicus
-
IC50 value is 0.00014 mM
0.000155
N-arachidonyl maleimide
Homo sapiens
-
in 50 mM HEPES buffer, pH 8, 1 mM EDTA, and 10% dimethyl sulfoxide at 25C for 60 min
0.0000091
N-arachidonylmaleimide
Homo sapiens
-
native enzyme, in 50 mM Tris-HCl (pH 7.4) containing 8% DMSO, at room temperature
0.00003
N-arachidonylmaleimide
Rattus norvegicus
-
wild-type, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/ml bovine serum albumin, fatty acid-free
0.000046
N-arachidonylmaleimide
Rattus norvegicus
-
recombinant purified enzyme, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/mlL bovine serum albumin, fatty acid-free
0.000107
N-arachidonylmaleimide
Rattus norvegicus
-
mutant C242G, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/ml bovine serum albumin, fatty acid-free
0.00014
N-arachidonylmaleimide
Rattus norvegicus
-
membrane-bound MAGL
0.000442
N-arachidonylmaleimide
Rattus norvegicus
-
mutant C201G, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/ml bovine serum albumin, fatty acid-free
0.0049
N-arachidonylmaleimide
Homo sapiens
-
using 2-oleoylglycerol as a substrate
0.0105
N-arachidonylmaleimide
Homo sapiens
-
using 4-nitophenyl acetate as a substrate
5.38
N-arachidonylmaleimide
Homo sapiens
-
mutant C201A, at 37C for 10 min, pH 8.0, in 50 mM Tris buffer
6.11
N-arachidonylmaleimide
Homo sapiens
-
mutant C242A, at 37C for 10 min, pH 8.0, in 50 mM Tris buffer
6.27
N-arachidonylmaleimide
Homo sapiens
-
wild-type, at 37C for 10 min, pH 8.0, in 50 mM Tris buffer
6.48
N-arachidonylmaleimide
Homo sapiens
-
mutant C208A/C242A, at 37C for 10 min, pH 8.0, in 50 mM Tris buffer
6.64
N-arachidonylmaleimide
Homo sapiens
-
mutant C208A, at 37C for 10 min, pH 8.0, in 50 mM Tris buffer
0.005
N-benzoylthiocarbamic cyclohexylethyl ester
Homo sapiens
-
using 4-nitophenyl acetate as a substrate
0.02
N-benzoylthiocarbamic cyclohexylethyl ester
Homo sapiens
-
using 2-oleoylglycerol as a substrate
0.051
N-cyclohexylmaleimide
Rattus norvegicus
-
IC50 value is 0.051 mM
0.0027
N-ethylmaleimide
Rattus norvegicus
-
recombinant purified enzyme, for 10 min at 37C, in 50 mM Tris-HCl, pH 8.0, 0.5 mg/ml bovine serum albumin, fatty acid-free
0.028
N-ethylmaleimide
Homo sapiens
-
-
0.413
N-hydroxymaleimide
Rattus norvegicus
-
IC50 value is 0.413 mM
0.00015
N-n-heptyl benzodioxaphosphorin oxide
Mus musculus
-
IC50 is 150 nM
0.044
N-Phenylmaleimide
Rattus norvegicus
-
IC50 value is 0.044 mM
0.053
N-propylmaleimide
Rattus norvegicus
-
IC50 value is 0.053 mM
0.1
N-[3-(4-fluorophenyl)-6-oxopyrazolo[5,1-c]pyrido[4,3-e][1,2,4]triazin-7(6H)-yl]-2-(naphthalen-2-yloxy)acetamide
Homo sapiens
-
IC50 above 0.1 mM, pH and temperature not specified in the publication
0.00001
N-[4-(1,3-benzothiazol-2-yl)phenyl]-2-(1H-benzotriazol-1-yl)acetamide
Homo sapiens
-
pH and temperature not specified in the publication
0.053
NEM
Rattus norvegicus
-
IC50 value is 0.053 mM
0.036
noladin ether
Rattus norvegicus
-
IC50 value is 0.036 mM
0.00015
O-n-octyl benzodioxaphosphorin oxide
Mus musculus
-
IC50 is 150 nM
0.00014
octane-1-sulfonyl fluoride
Mus musculus
-
-
0.00014
octyl sulfonyl fluoride
Mus musculus
-
IC50 is 140 nM
0.0023
Paraoxon
Mus musculus
-
IC50 is 0.0023 mM
0.000093
pristimerin
Rattus norvegicus
-
purified MGL, at pH 7.5, 37C
0.000398
pristimerin
Rattus norvegicus
-
nonpurified MGL, at pH 7.5, 37C
0.004
pristimerol
Rattus norvegicus
-
purified MGL, at pH 7.5, 37C
0.0000029
S-heptyl benzodioxaphosphorin oxide
Mus musculus
-
IC50 is 2.9 nM
0.31
S-nonyl benzodioxaphosphorin oxide
Mus musculus
-
IC50 is 0.31 nM
0.00000031
S-nonylbenzodioxaphosphorin oxide
Rattus norvegicus
-
cytosolic MAGL
0.0000031
S-pentyl benzodioxaphosphorin oxide
Mus musculus
-
IC50 is 3.1 nM
0.031
SPB 01403
Rattus norvegicus
-
-
0.000051
stearyl benzodioxaphosphorin oxide
Mus musculus
-
IC50 is 51 nM
0.00046
tetrahydrolipstatin
Homo sapiens
-
-
0.00041
troglitazone
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0011
troglitazone
Homo sapiens
-
pH and temperature not specified in the publication
0.0031
URB602
Homo sapiens
-
in 50 mM HEPES buffer, pH 8, 1 mM EDTA, and 10% dimethyl sulfoxide at 25C for 60 min
0.028
[1,1'-biphenyl]-3-yl-carbamic acid, cyclohexyl ester
Rattus norvegicus
-
cytosolic MAGL
0.075
[1,1'-biphenyl]-3-yl-carbamic acid, cyclohexyl ester
Rattus norvegicus
-
MAGL expressed in HeLa cells
0.00048
[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]carbamic acid benzyl ester
Homo sapiens
-
at 37C, pH 7.0, incubation time of 15 min, in the presence of 0.2% (m/v) Triton X-100
0.00061
[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]carbamic acid benzyl ester
Homo sapiens
-
at 37C, pH 7.0, incubation time of 15 min, without Triton X-100
0.0011
[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]carbamic acid benzyl ester
Homo sapiens
-
at 37C, pH 7.0, incubation time of 15 min, in the presence of 0.2% (m/v) Triton X-100
0.0000002
[4-[bis(1,3-benzodioxol-5-yl)methyl]-1-piperidinyl](1H-1,2,4-triazol-1-yl)methanone
Homo sapiens
-
at pH 7.4 and 37C
0.000003
methyl octylphosphonofluoridate
Rattus norvegicus
-
cytosolic MAGL
additional information
additional information
Homo sapiens
-
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0298
-
with 1(3)-arachidonoylglycerol as substrate
0.0318
-
with 2-arachidonoylglycerol as substrate
2.04
-
cytosolic fraction
29
-
crude enzyme, using olive oil as substrate, at pH 7.4, 30C
80
-
recombinant enzyme, using monomyristin as substrate, at 37C and at pH 8.0 in 2.5 mM Tris-HCl buffer, 150 mM NaCl, and 3 mM sodium taurodeoxycholate
121.1
-
-
143
-
recombinant enzyme, using monomyristin as substrate, at 37C and at pH 8.0 in 2.5 mM Tris-HCl buffer, 150 mM NaCl, and 3 mM sodium taurodeoxycholate
179
-
after 6.2fold purification, using olive oil as substrate, at pH 7.4, 30C
290
-
purified recombinant enzyme
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.5
-
phospholipase A2 activity
6 - 8
-
-
7.4
-
assay at
8
-
lipase activity
8
-
assay at
8
-
assay at
8.8
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5 - 9.5
-
pH 5.0: about 55% of maximal activity, pH 9.5: about 85% of maximal activity, enzyme from cytosol
6 - 9
-
50% of maximal activity at pH 6.5, no activity below pH 6.0, maximal activity at pH 7.5-9.0
6 - 9.5
-
pH 6.0: about 45% of maximal activity, pH 9.5: about 65% of maximal activity, enzyme from plasma membrane
8 - 10
-
activity peak of 7-hydroxycoumarinyl-arachidonate hydrolysis by MAGL
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
-
assay at
25
-
assay at
37
-
assay at
37
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.7 - 4.8
-
isoelectric focusing, pH gradient 3.5-10
4.7 - 4.8
isoelectric focusing
additional information
-
-
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Mus musculus C57BL/6
-
-
-
Manually annotated by BRENDA team
-
adrenal chromaffin cells
Manually annotated by BRENDA team
-
2 isozymes from alternative slicing
Manually annotated by BRENDA team
-
MGL is localized to axon terminals throughout the brain
Manually annotated by BRENDA team
-
MGL is expressed in central and peripheral axons of the fetal nervous system by embryonic day 12.5. MGL coexists with sn-1-diacylglycerol lipase alpha and CB1 cannabinoid receptors in corticofugal axons of pyramidal cells
Manually annotated by BRENDA team
Rattus norvegicus Sprague-Dawley
-
-
-
Manually annotated by BRENDA team
-
MGL and CB1 cannabinoid receptors are coexpressed in corticofugal but not thalamocortical axons
Manually annotated by BRENDA team
Rattus norvegicus Sprague-Dawley
-
-
-
Manually annotated by BRENDA team
-
proximal and distal colon
Manually annotated by BRENDA team
-
enzyme activity level is highest in duodenum
Manually annotated by BRENDA team
-
expressed in nerve cell bodies and nerve fibres of the enteric nervous system
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
-
-
Manually annotated by BRENDA team
-
ditributed in the muscle and mucosal layers of the ileum
Manually annotated by BRENDA team
-
liver MGL mRNA, protein and activity all increased 5-10-fold during development
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
liver MGL mRNA, protein and activity all increased 5-10-fold during development
-
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
-
-
Manually annotated by BRENDA team
-
mucosa, post-transcriptional regulation of expression, the enzyme expression is also developmentally regulated, quantitative RT-PCR analysis, overview
Manually annotated by BRENDA team
-
high expression in intestine
Manually annotated by BRENDA team
Mus musculus C57BL/6
-
mucosa, post-transcriptional regulation of expression, the enzyme expression is also developmentally regulated, quantitative RT-PCR analysis, overview
-
Manually annotated by BRENDA team
-
neuron enriched cultures from fetal spinal cord
Manually annotated by BRENDA team
additional information
-
Bv-2 cells do not express MAGL mRNA
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Mus musculus C57BL/6
-
presynaptic enzyme
-
Manually annotated by BRENDA team
-
after expression in HeLa cells
Manually annotated by BRENDA team
Rattus norvegicus Sprague-Dawley
-
-
-
Manually annotated by BRENDA team
Rattus norvegicus Sprague-Dawley
-
-
-
Manually annotated by BRENDA team
-
after expression in HeLa cells
Manually annotated by BRENDA team
additional information
-
immunolocalization studies
-
Manually annotated by BRENDA team
additional information
-
immunolocalization studies
-
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
19490
calculated from amino acid sequence
651084
20500
SDS-PAGE
651084
27400
calculated from amino acid sequence
651780
28000
SDS-PAGE
651780
33370
-
calculated from amino acid sequence
650849, 653676
34120
-
calculated from amino acid sequence
691733
35000
-
two isoforms of 35000 Da and 37000 Da, SDS-PAGE
650849
35000
-
two closely related isoforms of 35000 Da and 37000 Da, SDS-PAGE
653676
35000
-
SDS-PAGE
691733, 693868
37000
-
two isoforms of 35000 Da and 37000 Da, SDS-PAGE
650849
37000
-
two closely related isoforms of 35000 Da and 37000 Da, SDS-PAGE
653676
59000
-
SDS-PAGE
652586
63000
-
gel filtration
94273
68000
-
gel filtration
94267
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 30000, SDS-PAGE
?
-
x * 35000, brain splicing variant isozyme 1, SDS-PAGE, x * 37000, brain splicing variant isozyme 1, SDS-PAGE
?
-
x * 30223, detagged enzyme, MALDI-TOF mass spectrometry
?
-
x * 33000, MAGL-His6 protein, SDS-PAGE
?
-
x * 29882, calculated from amino acid sequence; x * 30000, recombinant enzyme, SDS-PAGE
?
-
x * 10965, MALDI-TOF mass spectrometry; x * 11000, SDS-PAGE
?
-
x * 33000, SDS-PAGE
?
-
x * 33218, calculation from nucleotide sequence
?
-
x * 45000, SDS-PAGE
?
-
x * 32900, SDS-PAGE
?
-
x * 60000-75000, SDS-PAGE
?
Mortierella alliacea YN-15
-
x * 10965, MALDI-TOF mass spectrometry; x * 11000, SDS-PAGE
-
?
Mycobacterium smegmatis mc2155
-
x * 29882, calculated from amino acid sequence; x * 30000, recombinant enzyme, SDS-PAGE
-
?
-
x * 30223, detagged enzyme, MALDI-TOF mass spectrometry
-
dimer
-
mass spectrometry
monomer
-
1 * 35000, SDS-PAGE
monomer
-
1 * 34178, calculated from amino acid sequence; 1 * 35000, SDS-PAGE
monomer
-
1 * 70000, SDS-PAGE
monomer
-
1 * 62000, SDS-PAGE
additional information
-
structure molecular modeling from amino acid sequence
additional information
-
enzyme molecular modeling, overview
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, using 1.5 M ammonium sulfate, 100 mM citrate (pH 5.8) and 100 mM tartrate
-
sitting drop vapor diffusion method, using 0.1 M MES/imidazole pH 6.5, 12.5% (w/v) PEG 1000, 12.5% (w/v) PEG 3350, 12.5% (w/v) MPD
-
sitting drop vapor diffusion method, using 0.1 M MES/imidazole, pH 6.5, 12.5% (w/v) PEG 1000, 12.5% (w/v) PEG 3350, 12.5% (w/v) 2-methyl-2,4-pentanediol or hanging drop vapor diffusion method using 0.1 M citric acid, pH 5.2, and 18% (w/v) PEG3350
-
hanging drop vapor diffusion method, benzamidine is essential for crystallization
-
apoenzyme alone or in complex with inhibitor SAR629, in 50 mM MES (pH 6.0) and 40% (v/v) 2-methyl-pentane-2,4-diol, at 4C
-
by the hanging drop method and under oil crystallization, native enzyme or selenomethionyl derivative, at 2.2 A resolution. Belongs to I222 space group, with two molecules per asymmetric unit. Docking of 2-arachidonoylglycerol highlights a hydrophobic and a hydrophilic cavity that accommodate the lipid into the catalytic site
-
in complex with methyl arachidonyl fluorophosphonate, hanging drop vapor diffusion method, using 6-10% (w/v) PEGMME 5000, 100 mM Na-MES pH 6.0, 0.2% (w/v) glucopyranoside, at 22C
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4
-
irreversible inactivation
94262
4 - 9
-
highly stable from pH 6.5 to 9.0 during 1 h of incubation. The enzyme shows a residual activity of 50% after 1 h of incubation at pH 4.0
715369
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4
-
half-life: 9 days
94271
21
-
half-life: 36 h
94271
37
-
half-life: 9 h
94271
45
wild-type enzyme is stable, A76G mutant loses 50% activity after 8 min
651084
45
-
15 min, more than 60% loss of activity
94267
55
-
15 min, complete inactivation
94267
58
-
the midpoint of the melting transition is calculated to be 58C for wild type enzyme
716864
60
-
stable for 10 min
651765
60
stable below
651780
65
-
stable for 1h
652586
70
-
80% activity after 1h
652586
70
-
the enzyme is completely inactivated when preincubated for 1 h at over 70C
716353
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80C, 50 mM Tris buffer, 200 mM NaCl, 0.1% lauryl dimethylamine N-oxide, pH 9.5
-
4C, 8 mM CHAPS, 5-7% loss of activity per day
-
-20C, 20% glycerol, 2 weeks, 25% loss of activity of the plasma membrane enzyme, no loss of activity of the cytosolic enzyme
-
-70C, 20 mM Tris-HCl or phosphate buffer, pH 7.0, 1 mM dithiothreitol, 1 mM EDTA, 0.2% C13E12, stable for several months
-
0C, stable for 2 weeks
-
4C, 20 mM Tris-HCl or phosphate buffer, pH 7.0, 1 mM dithiothreitol, 1 mM EDTA, 0.2% C13E12, half-life: 9 days
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni-NTA agarose column chromatography and Superdex 200 gel filtration
-
octyl-Sepharose column chromatography, cation exchange column chromatography, and gel filtration
-
separation of bovine brain monoacylglycerol lipase and diacylglycerol lipase by heparin Sepharose affinity chromatography
-
by a combination of streptactin and ion metal affinity chromatography
-
His-Trap column chromatography and Superdex 200 gel filtration
-
immobilized metal affinity chromatography
-
immobilized metal affinity column chromatography
-
MAGL-His6 protein purified on nickel-nitrilotriacetic acid column, more than 90% pure
-
Ni-Sepharose column chromatography and Superdex 75 gel filtration
-
recombinant His6-tagged and streptavidin-tagged enzyme from Escherichia coli to homogeneity by Strep-tag targeting afffinity chromatography and nickel affinity chromatography
-
Talon metal affinity resin chromatography
-
TALON metal affinity resin column chromatography
-
acetone precipitation, phenyl-Sepharose column chromatography, and Superdex 200 gel filtration
-
Ni-NTA column chromatography and Superdex 200 gel filtration
-
recombinant His-tagged wild-type and mutant enzymes from Escherichia coli by nickel affinity chromatography and gel filtration, removal of the His-tag
-
by gel filtration
-
partially purified
-
HisTrap column chromatography, gel filtration
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
expressed in Escherichia coli BL21(DE3) cells
-
expressed in Escherichia coli
-
expressed in Escherichia coli BL21 (DE3) cells
-
expressed in Escherichia coli BL21 and Rosetta cells. Expression in the baculovirus expression system produced only insoluble, aggregated protein
-
expressed in Escherichia coli BL21(DE3) cells
-
expressed in HEK-293 cells
-
functional overexpression of His6-tagged and streptavidin-tagged enzyme in Escherichia coli as soluble protein in the supernatant
-
functional overexpression of Rattus norvegicus brain enzyme in HeLa cells
-
into vector pColdII with a His6 tag at the N-terminus. Expression in Escherichia coli BL21 (DE3) competent cells
-
mutant enzymes are expressed in Escherichia coli BL21 (DE3) cells
-
wild-type and mutants expressed in the Escherichia coli Rosetta strain
-
expressed in Escherichia coli
-
expression in COS cells
-
quantitative RT-PCR for analysis of intestinal MGL mRNA expression
-
expressed in Escherichia coli Rosetta(DE3)/pLysS cells
-
gene Rv0183, DNA and amino acid sequence determination and anaylsis, expression of His-tagged wild-type and mutant enzymes in Escherichia coli
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expressed in COS-7 and HeLa cells
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expressed in HeLa cells
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full-length cDNA subcloned into the pEF15b vector containing an N-terminal histidine tag and transformed in Escherichia coli DH5alpha. Positive clones expressed in Escherichia coli Rosetta 2(De3)pLysS cells. Expression of wild-type and mutants in HeLa cells
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functional overexpression of the enzyme in HeLa cells
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HeLa cells transiently transfected with pEF6 vector containing full-length ABHD6 or ABHD12
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expressed in Escherichia coli BL21(DE3) cells
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
monoacylglycerol lipase is highly expressed in aggressive human cancer cells and primary tumors
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A76G
reduced thermostability, increased stability at pH 5-7, substitution converts the esterase into a monoacylglycerol hydrolase
C201A
-
substantial decrease in the inhibitory potential
C201A
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the mutation causes a significant reduction in overall activity particularly skewing the balanced hydrolysis of monoacyl glycerol isomers to favor the 2-isomer over the 1-isomer
C201A/C208A/C242A
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no significant inhibition by N-arachidonylmaleimide
C208A
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increase in the inhibiting power of N-arachidonylmaleimide
C208A
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the mutation does not affect enzyme catalytic activity
C208A
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the mutation causes a significant reduction in overall activity particularly skewing the balanced hydrolysis of monoacyl glycerol isomers to favor the 2-isomer over the 1-isomer
C208A/C242A
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increase in the inhibiting power of N-arachidonylmaleimide
C215A
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the mutation does not affect MGL hydrolytic activity and displays heightened N-arachidonylmaleimide sensitivity
C215A/C249A
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the mutation does not affect MGL hydrolytic activity
C242A
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very slight decrease in N-arachidonylmaleimide inhibitory potency
C242A
-
the mutation does not affect enzyme catalytic activity
C242A
-
the mutation causes a significant reduction in overall activity particularly skewing the balanced hydrolysis of monoacyl glycerol isomers to favor the 2-isomer over the 1-isomer
C249A
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the mutation does not affect MGL hydrolytic activity and displays reduced N-arachidonylmaleimide sensitivity
D239T
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the mutation substantially compromises enzyme activity
L167Q/L171Q
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the mutant shows increased catalytic efficiency with 4-methylumbelliferyl butyrate compared to the wild type enzyme
L167Q/L174Q
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the mutant shows increased catalytic efficiency with 4-methylumbelliferyl butyrate compared to the wild type enzyme
L169S/L176S
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the mutant shows reduced catalytic efficiency with 4-methylumbelliferyl butyrate and increased catalytic efficiency with umbelliferyl arachidonate compared to the wild type enzyme; the mutant shows reduced catalytic efficiency with 4-methylumbelliferyl butyrate compared to the wild type enzyme
L169S/L176S/K160A
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the mutant shows reduced catalytic efficiency with 4-methylumbelliferyl butyrate compared to the wild type enzyme
L169S/L176S/K165A
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the mutant shows reduced catalytic efficiency with 4-methylumbelliferyl butyrate compared to the wild type enzyme
L169S/L176S/K226A
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the mutant shows reduced catalytic efficiency with 4-methylumbelliferyl butyrate compared to the wild type enzyme
L169S/L176S/K36A
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the mutant shows about wild type catalytic efficiency with 4-methylumbelliferyl butyrate
L169S/L176S/K36A/K226A
-
the mutant shows reduced catalytic efficiency with 4-methylumbelliferyl butyrate compared to the wild type enzyme
L171Q
-
the mutant shows about wild type catalytic efficiency with 4-methylumbelliferyl butyrate
Y194A
-
the mutation causes a significant reduction in overall activity
Y194A/C242A
-
the mutation causes a significant reduction in overall activity
S111A
-
inactive
S111A
Mycobacterium smegmatis mc2155
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inactive
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D226A
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site-directed mutagenesis, active site residue mutation, the catalytic activity is affected
D226N
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site-directed mutagenesis, active site residue mutation, the catalytic activity is affected
H256A
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site-directed mutagenesis, active site residue mutation, the catalytic activity is affected
S110A
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site-directed mutagenesis, active site residue mutation, the catalytic activity is affected
D226A
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site-directed mutagenesis, active site residue mutation, the catalytic activity is affected
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D226N
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site-directed mutagenesis, active site residue mutation, the catalytic activity is affected
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H256A
-
site-directed mutagenesis, active site residue mutation, the catalytic activity is affected
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S110A
-
site-directed mutagenesis, active site residue mutation, the catalytic activity is affected
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C201G
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causes significant decreases in enzyme activity, albeit smaller than that produced by mutant C242G. Inhibitory potency of N-arachidonylmaleimide is selectively decreased
C208G
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causes significant decreases in enzyme activity, albeit smaller than that produced by mutant C242G. Inhibitory potency of octhilinone is selectively decreased. Has no effect on the inhibitory potency of N-arachidonylmaleimide
C242G
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produces a striking reduction in MGL activity, due to a decrease in maximal reaction velocity rather than a change in Michaelis constant. Inhibitory potency of N-arachidonylmaleimide is selectively decreased
C301G
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has no effect on MGL activity
C32G
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has no effect on MGL activity
C55G
-
has no effect on MGL activity
L171Q/L174Q
-
the mutant shows increased catalytic efficiency with 4-methylumbelliferyl butyrate compared to the wild type enzyme
additional information
-
construction of a HeLa cell line, HeLa-MGLi, with stable repression of enzyme expression by RNAi silencing, the cells show 20% of wild-type cell line enzyme activity
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug development
-
the enzyme is a target for design of potent and selective inhibitors
drug development
-
structure of MAGL paves the way for future medicinal chemistry works aimed at the design of new drugs exploiting 2-arachidonoylglycerol transmission. MAGL is a hot therapeutic target, because the design of selective and potent inhibitors can provide unique tools to interfere with 2-arachidonoylglycerol degradation and to finely modulate the endocannabinoid signal
drug development
-
potent MGL inhibitors with selectivity over FAAH may be realized by exploiting structural difference as well as the binding sub-pocket, increased volume around the catalytic site, and potential hydrogen-bonding opportunities
pharmacology
-
the enzyme is a therapeutic target
synthesis
-
the highly stable Mortierella alliacea lipase may be useful for the synthesis of structured lipids, particularly acylglycerols containing functional unsaturated fatty acids at the sn-2 position
synthesis
Mortierella alliacea YN-15
-
the highly stable Mortierella alliacea lipase may be useful for the synthesis of structured lipids, particularly acylglycerols containing functional unsaturated fatty acids at the sn-2 position
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drug development
-
selective inhibitors of MGL may be valuable novel agents for the treatment of inflammatory pain. (2S,9Z)-octadec-9-ene-1,2-diamine is a selective inhibitor of MGL activity with in vivo analgesic and anti-inflammatory properties
medicine
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MGL represents a target for the treatment of inflammatory pain