3.5.1.23: ceramidase
This is an abbreviated version!
For detailed information about ceramidase, go to the full flat file.
Word Map on EC 3.5.1.23
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3.5.1.23
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adipor1
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sphingolipids
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obesity
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adipokine
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agonist
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sphingomyelinase
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sphingomyelin
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lysosomal
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farber
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obese
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leptin
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adipocytes
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amp-activated
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sphingosine-1-phosphate
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peroxisome
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cardiovascular
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proliferator-activated
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triglyceride
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globular
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insulin-sensitizing
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high-fat
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tnf
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smases
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adipocytokine
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adipocyte-derived
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monophosphate-activated
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anti-atherogenic
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t-cadherin
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steatosis
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adiposity
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glucosylceramide
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glycosphingolipids
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obesity-related
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antidiabetic
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1-phosphate
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seven-transmembrane
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gaucher
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dihydrosphingosine
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p-ampk
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palmitoyltransferase
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homa-ir
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sphingoid
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hoarseness
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ceramide-induced
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sphinganine
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ceramide-mediated
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dihydroceramide
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myoclonic
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adipocyte-secreted
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analysis
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pharmacology
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drug development
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medicine
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hypoadiponectinemia
- 3.5.1.23
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adipor1
- sphingolipids
- obesity
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adipokine
- agonist
- sphingomyelinase
- sphingomyelin
- lysosomal
- farber
-
obese
- leptin
- adipocytes
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amp-activated
- sphingosine-1-phosphate
- peroxisome
- cardiovascular
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proliferator-activated
- triglyceride
-
globular
-
insulin-sensitizing
-
high-fat
- tnf
- smases
-
adipocytokine
-
adipocyte-derived
-
monophosphate-activated
-
anti-atherogenic
-
t-cadherin
- steatosis
-
adiposity
- glucosylceramide
- glycosphingolipids
-
obesity-related
-
antidiabetic
- 1-phosphate
-
seven-transmembrane
- gaucher
- dihydrosphingosine
-
p-ampk
- palmitoyltransferase
-
homa-ir
-
sphingoid
- hoarseness
-
ceramide-induced
- sphinganine
-
ceramide-mediated
- dihydroceramide
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myoclonic
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adipocyte-secreted
- analysis
- pharmacology
- drug development
- medicine
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hypoadiponectinemia
Reaction
Synonyms
(dihydro)ceramidase, AC, aCDase, ACER, ACER type 3, ACER-2, ACER1, ACER2, ACER3, acid ceramidase, acylsphingosine deacylase, adiponectin receptor, ADIPOR2, alkaline ceramidase, alkaline ceramidase 1, alkaline ceramidase 2, alkaline ceramidase 3, alkCDase, alkCDase-1, alkCDase-2, ASAH-1, ASAH1, asah1b, ASAH2, ASAH2B, ASAH3, AsahA, AtACER, AtNCER1, bwa, CBCDase, CDase, CDase II, CER2, ceramidase, Dacer, Drosophila alkaline ceramidase, glycosphingolipid ceramide deacylase, Golgi alkaline ceramidase, haCER1, intramembrane ceramidase, LsnCer, maCER1, mt-CDase, N-acylsphingosine amidohydrolase, N-acylsphingosine amidohydrolase 2, N-acylsphingosine amidohydrolase-1, N-acylsphingosine aminohydrolase, N-acylsphingosine deacylase, N-CDase, nCDase, ncer1, neutral CDase, neutral ceramidase, neutral ceramidase 2, NlnCDase, OsCDase, PaCD, PaCDase, pan-ceramidase, PHP32, phytoalkaline ceramidase, phytoCDase, Putative 32 KDA heart protein, SCDase, sphingolipid ceramide N-deacylase, Tncer, TOD1, turgor regulation defect 1, Ydc1p, yeast dihydroceramidase 1, yeast phyto-ceramidase 1, Ypc1p, znCD
ECTree
3.5.1.23 ceramidaseAdvanced search results
results (
results (Inhibitors
Inhibitors on EC 3.5.1.23 - ceramidase
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INHIBITOR 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
IMAGE
(1R, 2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
inhibits in vitro
(1R,2R)-2-N-(tetradecanoylamino)-1-(4'-nitrophenyl)-propyl-1,3-O,O-(N,N-dimethylamino)acetate dihydrochloride
i.e. LCL521 or Di-DMG-B13, is a lysosomotropic inhibitor of ACDase, inhibition mechanism, overview. Low dose of LCL521 (0.001 mM) effectively inhibits ACDase in cells, but the effects are transient. A higher dose of LCL521 (0.01 mM) causes profound decrease of sphingosine and increase of ceramide, but additionally affects the processing and regeneration of the ACDase protein, with biphasic and reversible effects on the expression of ACDase, which parallels the long term changes of cellular sphingosine and ceramide. Finally, the higher concentrations of LCL521 also inhibit dihydroceramide desaturase (DES-1, EC 1.14.19.17). LCL521 inhibits ACDase specifically among the ceramidases in vitro, which is reinforced by the lysosomal targeting
(1S, 2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
inhibitor of alkaline ceramidase; inhibitor of alkaline ceramidase; inhibitor of neutral ceramidase
(E)-4-[(2S,3R)-N-1,3-dihydroxyoctadecan-2-ylamino]4-oxo-2-butenoic acid
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1-ethyl-3-(3-dimethylaminopropyl)carbodiimide
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modification of carboxyl groups completely inhibits forward and reverse reaction
12-amino-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]dodecanamide
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2,3-Butanedione
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modification of Arg causes about 50% inhibition of forward and reverse reaction
3-(6-phenylhexanoyl)-1,3-oxazolidin-2-one
above, pH and temperature not specified in the publication, 9.4% inhibition at 0.02 mM
3-(cyclopropylmethyl)-5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
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3-[4-(cyclohexyloxy)benzoyl]-1,3-oxazolidin-2-one
above, pH and temperature not specified in the publication, 18.3% inhibition at 0.02 mM
3-[6-(3-chlorophenyl)hexanoyl]-1,3-oxazolidin-2-one
above, pH and temperature not specified in the publication, 14.7% inhibition at 0.02 mM
3-[6-(4-hydroxyphenyl)hexanoyl]-1,3-oxazolidin-2-one
above, pH and temperature not specified in the publication, 4.9% inhibition at 0.02 mM
5-chloro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
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5-fluoro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
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5-fluoro-N-hexyl-3-(2-methylpropanoyl)-2,4-dioxopyrimidine-1-carboxamide
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6-(4-fluorophenyl)-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide
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6-(4-fluorophenyl)-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide}
in vivo plasma pharmacokinetic profile in mice, overview
6-chloro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
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cardiolipin
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inhibits the ceramide synthesis activity: total inhibition at 2.5-5 mol%, activates the ceramidase activity, mechanism
Ceranib-1
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i.e. 3-(3-(4-methoxyphenyl)acryloyl)-6-methyl-4-phenylquinolin-2(1H)-one
cholesterol
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0.08 mM or below, decreases the hydrolysis of ceramide by a maximum of two-thirds
D-erythro-urea-C16-ceramide
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mtCDase, competitive inhibition, IC50: 0.33 mol%
ethyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
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isobutyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
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LCL521
a lysosomotropic prodrug inhibitor of acid ceramidase, inhibition in vivo leads to decreased cell viability
lysophosphatidylcholine
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ceramide synthesis activity, 10 mol%, moderate inhibition
methyl 5-fluoro-3-(hexylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
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methyl 5-fluoro-3-(octylcarbamoyl)-2,6-dioxopyrimidine-1-carboxylate
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myristaldehyde
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competitively inhibits the ceramide synthesis activity, 2.5-3 mol%, about 50% inhibition
N-bromosuccinimide
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modification of Trp completely inhibits forward and reverse reaction
N-hexyl-2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidine-1(2H)-carboxamide
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N-hexyl-5,6-dimethyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
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N-hexyl-5-(4-methylpiperazin-1-yl)-2,4-dioxopyrimidine-1-carboxamide
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N-hexyl-5-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
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N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]-12-(dimethylamino)dodecanamide
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N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]dodecane-1-sulfonamide
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N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]tridecan-1-aminium chloride
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N-[(1R,2R)-1,3-dihydroxy-1-phenylpropan-2-yl]tridecan-1-aminium chloride
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N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-12-(1-methylhydrazinyl)dodecanamide
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N-[(1S,2R)-1-hydroxy-1-(4-nitrophenyl)propan-2-yl]dodecane-1-sulfonamide
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N-[(2R)-2-hydroxy-2-(pyridin-3-yl)ethyl]-12-(1-methylhydrazinyl)dodecanamide
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N-[(2R)-2-hydroxy-2-(pyridin-4-yl)ethyl]-12-(1-methylhydrazinyl)dodecanamide
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N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]2,2-dibromoacetamide
strong inhibition
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]2-bromoacetamide
strong inhibition
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]2-methylacrylamide
strong inhibition
N-[(2S,3R,4E)-14-azido-1,3-dihydroxytetradec-4-en-2-yl]-2-bromoacetamide
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N-[2-hydroxy-2-(pyridin-3-yl)ethyl]-12-(1-methylhydrazinyl)dodecanamide
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palmitaldehyde
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ceramide synthesis activity, 2.5-3 mol%, about 50% inhibition
phorbol myristate acetate
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phorbol myristate acetate, PMA, decreases the expression of ACER2 in HeLa cells
phosphatidylglycerol
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ceramide synthesis activity, 10 mol%, moderate inhibition
(1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
potent inhibitor of acid ceramidase
(1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
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(1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
the efficacy of (1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol in vitro as well as in intact cells can be enhanced by suitable modification of functional groups; the efficacy of the inhibitor in vitro as well as in intact cells can be enhanced by suitable modification of functional groups
(1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol
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(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
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i.e. D-e-MAPP, an alkaline ceramidase inhibitor, that potently and specifically inhibits ACER1, ACER2, and ACER3 activity
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
inhibits in vitro
(1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
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i.e. D-e-MAPP, an alkaline ceramidase inhibitor, that potently and specifically inhibits ACER activity
2-mercaptoethanol
-
inhibits both ceramidase and ceramide synthesis activity
carmofur
a drug used in treatment of colorectal cancers and a potent in vivo active inhibitor of intracellular acid ceramidase activity. The potent noncompetitive inhibitor enzyme inhibitor has is anti-proliferative effects. Carmofur inhibits acid ceramidase and increases ceramide levels in human SW403 and LNCaP cells
carmofur
a specific ASAH1 inhibitor, inhibition by carmofur contributes to cytotoxicity
carmofur
a drug used in treatment of human colorectal cancers and a potent noncompetitive inhibitor in vivo active inhibitor of intracellular acid ceramidase activity
D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
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inhibitor of alkaline ceramidase
D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
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inhibitor of alkaline ceramidase
D-erythro-sphingosine
recombinant CDase, more inhibitory than L-erythro-sphingosine
D-erythro-sphingosine
-
IC50: 0.04 mol%, mt-CDase is inhibited by all stereoisomers of sphingosine with IC50 ranging from 0.04 to 0.14 mol%
di-isopropyl fluorophosphate
the substrate protects against inhibition
EDTA
recombinant CDase, complete inhibition, Ca2+ restores activity
EGTA
recombinant CDase, complete inhibition, Ca2+ restores activity
glycodeoxycholate
inhibits in vitro neutral ceramidase activity
L-erythro-sphingosine
recombinant CDase, 0.02 mM, 20% inhibition, less inhibitory than L-erythro-sphingosine
L-erythro-sphingosine
-
competitive inhibitor of ceramide synthesis activity
N-oleoylethanolamine
low potency, inhibitor of acid ceramidase
oleoylethanolamide
i.e. N-oleylethanolamine; i.e. N-oleylethanolamine
oleoylethanolamide
i.e. N-oleylethanolamine; i.e. N-oleylethanolamine
phosphatidic acid
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ceramide synthesis activity, 2.5-5 mol%, total inhibition
phosphatidylcholine
inhibitor of alkaline ceramidase; inhibitor of alkaline ceramidase; inhibitor of neutral ceramidase
phosphatidylcholine
-
ceramide synthesis activity, 10 mol%, moderate inhibition
phosphatidylserine
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ceramide synthesis activity, 10 mol%, moderate inhibition
taurocholate
inhibits in vitro neutral ceramidase activity
taurodeoxycholate
inhibits in vitro neutral ceramidase activity
Triton X-100
2fold activation at 0.1-0.2%, but inhibitory beyond the optimum concentration
additional information
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no inhibition by phosphatidylethanolamine, phosphatidylinositol, phosphatidylglycerol
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additional information
no inhibition by protease inhibitors such as aprotinin, PMSF, leupeptin, and pepstatin
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additional information
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no inhibition by protease inhibitors such as aprotinin, PMSF, leupeptin, and pepstatin
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additional information
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desipramine downregulates acid ceramidase in cancer cells, which is almost completely reversible by leupeptin and CA074ME, but not by pepstatin A, mechanism, overview
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additional information
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cellular ACER2 activity is inhibited by depletion of Ca2+ from Golgi lumen
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additional information
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all stereoisomers of D-erythro-ceramide and sphingosine (L-threo, D-threo, and L-erythro isomers), N-methyl-D-erythro-sphingosine and D-erythro-urea-C16-ceramide show significant inhibitory effects on neural ceramidase; N-methyl ceramide, 1-O-methyl ceramide, cis-D-erythro ceramide or N,N-dimethyl-D-erythrosphingosine have no effect on neutral ceramidase
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additional information
all stereoisomers of D-erythro-ceramide and sphingosine (L-threo, D-threo, and L-erythro isomers), N-methyl-D-erythro-sphingosine and D-erythro-urea-C16-ceramide show significant inhibitory effects on neural ceramidase; N-methyl ceramide, 1-O-methyl ceramide, cis-D-erythro ceramide or N,N-dimethyl-D-erythrosphingosine have no effect on neutral ceramidase
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additional information
all stereoisomers of D-erythro-ceramide and sphingosine (L-threo, D-threo, and L-erythro isomers), N-methyl-D-erythro-sphingosine and D-erythro-urea-C16-ceramide show significant inhibitory effects on neural ceramidase; N-methyl ceramide, 1-O-methyl ceramide, cis-D-erythro ceramide or N,N-dimethyl-D-erythrosphingosine have no effect on neutral ceramidase
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additional information
all stereoisomers of D-erythro-ceramide and sphingosine (L-threo, D-threo, and L-erythro isomers), N-methyl-D-erythro-sphingosine and D-erythro-urea-C16-ceramide show significant inhibitory effects on neural ceramidase; N-methyl ceramide, 1-O-methyl ceramide, cis-D-erythro ceramide or N,N-dimethyl-D-erythrosphingosine have no effect on neutral ceramidase
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additional information
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DMAPP has no affect on ceramidase activity up to at least 0.3 mM. N-oleoylethanolamine has no affect on ceramidase activity
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additional information
a class of benzoxazolone carboxamides act as the first potent and systemically active inhibitors of the acid ceramidase. Prototype members of this class inhibit the enzyme with low nanomolar potency by covalent binding to the catalytic cysteine. No inhibition by N-methyl-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide, 4-phenylbutyl 2-oxo-1,3-benzoxazole-3(2H)-carboxylate, and 3-(6-phenylhexanoyl)-1,3-benzoxazol-2(3H)-one, while 2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carbothioamide is unstable
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additional information
amide- and sulfonamide-based compounds as potential inhibitors of ceramidases, synthesis and inhibitory potencies, overview. The hydrophobicity and the steric effects of longer alkyl chains (n-Pr, n-Bu or t-Bu groups) at the phenyl ring are important for an enhanced selectivity towards acid ceramidase over neutral ceramidase
-
additional information
amide- and sulfonamide-based compounds as potential inhibitors of ceramidases, synthesis and inhibitory potencies, overview. The hydrophobicity and the steric effects of longer alkyl chains (n-Pr, n-Bu or t-Bu groups) at the phenyl ring are important for an enhanced selectivity towards acid ceramidase over neutral ceramidase
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additional information
structural modification of the known ceramidase inhibitors (1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol and N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]-12-(dimethylamino)dodecanamide generates more potent ceramidase inhibitors that are active in intact cells and not only elevates the cellular ceramide levels, but also enhances cell death
-
additional information
structural modification of the known ceramidase inhibitors (1R,2R)-2-(N-tetradecanoylamino)-1-(4-nitrophenyl)-1,3-propanediol and N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]-12-(dimethylamino)dodecanamide generates more potent ceramidase inhibitors that are active in intact cells and not only elevates the cellular ceramide levels, but also enhances cell death
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additional information
modifications in the chemical scaffold of carmofur yield acid ceramidase inhibitors that act synergistically with standard antitumoral drugs to prevent cancer cell proliferation, design of chemosensitizing agents, overview
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additional information
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modifications in the chemical scaffold of carmofur yield acid ceramidase inhibitors that act synergistically with standard antitumoral drugs to prevent cancer cell proliferation, design of chemosensitizing agents, overview
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additional information
synthesis of several analogues of SABRAC that are potent irreversible enzyme inhibitors by reaction with the active site Cys143, fluorescent SABRAC analogues are used for enzyme detection
-
additional information
not inhibited by Mg2+, phytosphingosine, dihydrosphingosine
-
additional information
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not inhibited by Mg2+, phytosphingosine, dihydrosphingosine
-
additional information
a class of benzoxazolone carboxamides act as the first potent and systemically active inhibitors of the acid ceramidase. Prototype members of this class inhibit the enzyme with low nanomolar potency by covalent binding to the catalytic cysteine. No inhibition by N-methyl-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carboxamide, 4-phenylbutyl 2-oxo-1,3-benzoxazole-3(2H)-carboxylate, and 3-(6-phenylhexanoyl)-1,3-benzoxazol-2(3H)-one, while 2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3(2H)-carbothioamide is unstable
-
additional information
not inhibited by 1 mM iodoacetic acid, 0.1 mM 2-mercaptoethanol, 0.05 mM hexadecylsulfonylfluoride, 1 mM p-phenylmethylsulfonylfluoride, 0.2 mM D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol, 0.5 mM N-oleoylethanolamine, L(-)- and D(-)-norephenedrin
-
additional information
-
not inhibited by N-methyl-hexadecanoyl-ceramide, 1-O-methyl-hexadecanoyl-ceramide, 3-O-methyl-hexadecanoyl-ceramide, cis-D-erythro-hexadecanoyl-ceramide, 3-O-methyl-D-erythro-sphingosine, requirements for inhibition of mtCDase
-
additional information
-
the ceramide synthesis activity is not inhibited in vitro and in cells by fuminosin B1, not inhibited by EDTA or ATP, both up to 10 mM
-
additional information
EDTA, Mn2+ and Mg2+ have little effect on activity of 112 kDa CDase from kidney
-
additional information
-
the enzyme is stable to trypsin and chymotrypsin exposure
-
additional information
no inhibition by protease inhibitors such as aprotinin, PMSF, leupeptin, and pepstatin
-
additional information
-
GMP, GDT, GTP, TDP, TTP, UDP, and UTP, ADP and AMP have no significant effects on the enzyme activity. S-1-P has no inhibitory effect
-
additional information
synthesis and evaluation of a series of 2,4-dioxopyrimidine-1-carboxamides as acid ceramidase enzyme inhibitors, structural features of uracil derivatives that are critical for inhibition, overview. No inhibition by 7 and 27b, while 4o, 26 and 30 are unstable
-
additional information
the reverse ceramidase activity in microsomes can only be blocked by a lysine residuespecific reagent when the reagent has access to Ypc1p from the lumenal side
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additional information
the reverse ceramidase activity in microsomes can only be blocked by a lysine residuespecific reagent when the reagent has access to Ypc1p from the lumenal side
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additional information
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the reverse ceramidase activity in microsomes can only be blocked by a lysine residuespecific reagent when the reagent has access to Ypc1p from the lumenal side
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