Information on EC 3.1.4.39 - alkylglycerophosphoethanolamine phosphodiesterase

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

EC NUMBER
COMMENTARY hide
3.1.4.39
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RECOMMENDED NAME
GeneOntology No.
alkylglycerophosphoethanolamine phosphodiesterase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
1-alkyl-sn-glycero-3-phosphoethanolamine + H2O = 1-alkyl-sn-glycerol 3-phosphate + ethanolamine
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of phosphoric ester
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
plasmalogen degradation
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Ether lipid metabolism
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SYSTEMATIC NAME
IUBMB Comments
1-alkyl-sn-glycero-3-phosphoethanolamine ethanolaminehydrolase
Also acts on acyl and choline analogues.
CAS REGISTRY NUMBER
COMMENTARY hide
62213-15-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
gene atx
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Manually annotated by BRENDA team
Loxosceles sp.
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1-alkyl-sn-glycero-3-phospho-L-serine + H2O
1-alkyl-sn-glycerol 3-phosphate + L-serine
show the reaction diagram
-
-
-
-
?
1-alkyl-sn-glycero-3-phosphocholine + H2O
1-alkyl-sn-glycero-3-phosphate + choline
show the reaction diagram
-
-
-
?
1-alkyl-sn-glycero-3-phosphocholine + H2O
1-alkyl-sn-glycerol 3-phosphate + choline
show the reaction diagram
1-alkyl-sn-glycero-3-phosphoethanolamine + H2O
1-alkyl-sn-glycero-3-phosphate + ethanolamine
show the reaction diagram
1-alkyl-sn-glycero-3-phosphoethanolamine + H2O
1-alkyl-sn-glycerol 3-phosphate + ethanolamine
show the reaction diagram
1-heptadecanoyl-sn-glycero-3-phosphocholine + H2O
1-heptadecanoyl-sn-glycerol 3-phosphate + choline
show the reaction diagram
1-linoleoyl-2-lyso-glycerophoshorylcholine + H2O
1-linoleoyl-sn-glycerol-3-phosphate + choline
show the reaction diagram
-
-
-
-
?
1-linoleoyl-sn-glycero-3-phosphocholine + H2O
1-linoleoyl-sn-glycerol 3-phosphate + choline
show the reaction diagram
1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine + H2O
1-O-alkyl-2-lyso-sn-glycero-3-phosphate + choline
show the reaction diagram
1-O-alkyl-2-lyso-sn-glycero-3-phosphoethanolamine + H2O
1-O-alkyl-2-lyso-sn-glycero-3-phosphate + ethanolamine
show the reaction diagram
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the microsomal enzyme
the microsomal enzyme
?
1-O-hexadecyl-2-lyso-glycerophosphorylcholine + H2O
1-O-hexadecyl-sn-glycerol-3-phosphate + choline
show the reaction diagram
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lysoPAF (alkyl-lysophosphatidylcholine), lysoPLD shows higher activity towards lysoPAF
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-
?
1-O-hexadecyl-2-lyso-sn-glycero-3-phosphocholine + H2O
1-O-hexadecyl-2-lyso-sn-glycero-3-phosphate + choline
show the reaction diagram
1-O-hexadecyl-2-lyso-sn-glycero-3-phosphoethanolamine + H2O
1-O-hexadecyl-2-lyso-sn-glycero-3-phosphate + ethanolamine
show the reaction diagram
1-O-octadecyl-2-lyso-sn-glycero-3-phosphocholine + H2O
1-O-octadecyl-2-lyso-sn-glycero-3-phosphate + choline
show the reaction diagram
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?
1-palmitoyl-2-lyso-glycerophoshorylcholine + H2O
1-palmitoyl-sn-glycerol-3-phosphate + choline
show the reaction diagram
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-
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?
1-palmitoyl-sn-glycero-3-phosphocholine + H2O
1-palmitoyl-sn-glycerol 3-phosphate + choline
show the reaction diagram
1-stearoyl-2-lyso-glycerophoshorylcholine + H2O
1-stearoyl-sn-glycerol-3-phosphate + choline
show the reaction diagram
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?
4-nitrophenyl thymidine 5'-phosphate + H2O
4-nitrophenol + thymidine 5'-phosphate
show the reaction diagram
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-
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?
4-nitrophenyl-TMP + H2O
4-nitrophenol + TMP
show the reaction diagram
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?
4-nitrophenyl-TMP + H2O
?
show the reaction diagram
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?
5-[[(23R)-33-(4-[[4-(dimethylamino)phenyl]diazenyl]phenyl)-20,23-dihydroxy-20-oxido-15,33-dioxo-3,6,9,12,19,21,25-heptaoxa-16,32-diaza-20-phosphatritriacont-1-yl]carbamoyl]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid + H2O
?
show the reaction diagram
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fluorogenic substrate analogue for lysophosphatidylcholine
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?
arachidoyl-lysophosphatidylcholine + H2O
1-arachidoyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
behenoyl-lysophosphatidylcholine + H2O
1-behenoyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
bis(4-nitrophenyl)phosphate + H2O
?
show the reaction diagram
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?
bis(para-nitrophenyl)phosphate + H2O
?
show the reaction diagram
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?
caproyl-lysophosphatidylcholine + H2O
1-hexanoyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
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?
capryl-lysophosphatidylcholine + H2O
1-decanoyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
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?
caprylyl-lysophosphatidylcholine + H2O
1-octanoyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
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?
coumarin-phosphate-fluorescein + H2O
?
show the reaction diagram
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?
CPF4 + H2O
?
show the reaction diagram
decanoyl-lysophosphatidylcholine + H2O
1-decanoyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
FS-2 + H2O
?
show the reaction diagram
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fluorogenic substrate analogue for lysophosphatidylcholine
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?
FS-3 + H2O
2-(6-hydroxy-3-oxo-9a,10a-dihydro-3H-xanthen-9-yl)-5-[(18-hydroxy-15-oxo-3,6,9,12-tetraoxa-16-azaoctadec-1-yl)carbamoyl]benzoic acid + (2R)-2-hydroxy-3-(phosphonooxy)propyl 6-[(4-[(E)-[4-(dimethylamino)phenyl]diazenyl]benzoyl)amino]hexanoate
show the reaction diagram
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fluorogenic lysoPLD substrate
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?
FS-3 + H2O
?
show the reaction diagram
hexanoyl-lysophosphatidylcholine + H2O
1-hexanoyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
lauroyl-lysophosphatidylcholine + H2O
1-lauroyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
lyso-phosphatidylcholine + H2O
lyso-phosphatidic acid + choline
show the reaction diagram
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central in some key metabolic deregulations
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?
lysoDDPB + H2O
?
show the reaction diagram
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synthesized by an enzyme-assisted strategy. Lysophosphatidylcholine analogue that contains a fluorescence quencher at each acyl chain terminus and a fluorophore appended to the phospholipid headgroup through a choline-mimetic linker
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?
lysophosphatidyl choline + H2O
lysophosphatidic acid + choline
show the reaction diagram
lysophosphatidylcholine + H2O
lysophosphatic acid + choline
show the reaction diagram
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LPC, purified enzyme hydrolyzes saturated forms of lysophosphatidylcholine more robustly than unsaturated forms
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?
lysophosphatidylcholine + H2O
lysophosphatidic acid + choline
show the reaction diagram
lysophosphatidylcholine 16:0 + H2O
?
show the reaction diagram
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?
lysophosphatidylcholine 18:0 + H2O
?
show the reaction diagram
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?
lysophosphatidylcholine 18:1 + H2O
?
show the reaction diagram
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?
myristoyl-lysophosphatidylcholine + H2O
1-myristoyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
octanoyl-lysophosphatidylcholine + H2O
1-octanoyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
oleoyl-lysophosphatidylcholine + H2O
1-oleoyl-sn-gycerol 3-phosphate + choline
show the reaction diagram
p-nitrophenyl phenylphosphate + H2O
p-nitrophenol + phenylphosphate
show the reaction diagram
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?
p-nitrophenyl thymidine 5'-monophosphate + H2O
?
show the reaction diagram
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?
palmitoyl-lysophosphatidylcholine + H2O
1-palmitoyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
platelet-activating factor + H2O
? + choline
show the reaction diagram
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PAF, same extent as palmityl-lysophosphatidylcholine
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?
sphingosylphosphorylcholine + H2O
sphingosine 1-phosphate + choline
show the reaction diagram
sphingosylphosphorylcholine + H2O
sphingosine-1-phosphate + choline
show the reaction diagram
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?
stearoyl-lysophosphatidylcholine + H2O
1-stearoyl-sn-gycerol-3-phosphate + choline
show the reaction diagram
[(11R)-1-(4-[(Z)-[4-(dimethylamino)phenyl]diazenyl]phenyl)-N-[3-[(5-[5-[(3,5-dimethyl-2H-pyrrol-2-ylidene-kappaN)methyl]-1H-pyrrol-2-yl-kappaN]pentanoyl)amino]propyl]-11,14-dihydroxy-N,N-dimethyl-1,8-dioxo-9,13,15-trioxa-2-aza-14-phosphaheptadecan-17-aminiumato 14-oxide](difluoro)boron(1+) + H2O
?
show the reaction diagram
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synthesized by an enzyme-assisted strategy. lysophosphatidylcholine analogue that contains a fluorescence quencher at each acyl chain terminus and a fluorophore append to the phospholipid headgroup through a choline-mimetic linker
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?
[(2R)-26-(4-[(Z)-[4-(dimethylamino)phenyl]diazenyl]phenyl)-2,5-dihydroxy-5-oxido-10,26-dioxo-4,6,13,16,19,22-hexaoxa-9,25-diaza-5-phosphahexacos-1-yl 6-[(5-[5-[(3,5-dimethyl-2H-pyrrol-2-ylidene-kN)methyl]-1H-pyrrol-2-yl-kappaN]pentanoyl)amino]hexanoatato](difluoro)boron + H2O
?
show the reaction diagram
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fluorogenic substrate analogue for lysophosphatidylcholine
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?
[5-[[(23S)-33-(4-[(E)-[4-(dimethylamino)phenyl]diazenyl]phenyl)-20,23-dihydroxy-20-oxido-15,26,33-trioxo-3,6,9,12,19,21,25-heptaoxa-16,32-diaza-20-phosphatritriacont-1-yl]carbamoyl]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)phenyl]acetic acid + H2O
?
show the reaction diagram
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second-generation fluorogenic autotaxin/lysoPLD substrate. The molecule consists of an ethanoamido head group linked to a dabcyl quencher via the amino group. The hydroxyl group of the head group is conjugated to fluorescein via a phosphodiester bond and a polyethylene glycol linker. [5-[[(23S)-33-(4-[(E)-[4-(dimethylamino)phenyl]diazenyl]phenyl)-20,23-dihydroxy-20-oxido-15,26,33-trioxo-3,6,9,12,19,21,25-heptaoxa-16,32-diaza-20-phosphatritriacont-1-yl]carbamoyl]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)phenyl]acetic acid is therefore a more lipid-like substrate than coumarin-phosphate-fluorescein
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
1-alkyl-sn-glycero-3-phosphocholine + H2O
1-alkyl-sn-glycerol 3-phosphate + choline
show the reaction diagram
1-alkyl-sn-glycero-3-phosphoethanolamine + H2O
1-alkyl-sn-glycerol 3-phosphate + ethanolamine
show the reaction diagram
1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine + H2O
1-O-alkyl-2-lyso-sn-glycero-3-phosphate + choline
show the reaction diagram
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may play a role in the metabolism of platelet-activating factor
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?
lysophosphatidyl choline + H2O
lysophosphatidic acid + choline
show the reaction diagram
Q13822
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?
lysophosphatidylcholine + H2O
lysophosphatidic acid + choline
show the reaction diagram
sphingosylphosphorylcholine + H2O
sphingosine 1-phosphate + choline
show the reaction diagram
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?
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
KSCN
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200 mM, 37% increase of activity
Na3VO4
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enzyme activity requires Na3VO4, not necessary after purification
NaCl
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200 mM, 37% increase of activity
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(5Z)-2-(4-ethylpiperazin-1-yl)-5-(4-fluorobenzylidene)-1,3-thiazol-4(5H)-one
93.8% inhibition at 0.01 mM
(5Z)-2-(azepan-1-yl)-5-(4-propoxybenzylidene)-1,3-thiazol-4(5H)-one
96.6% inhibition at 0.01 mM
(5Z)-2-(morpholin-4-yl)-5-[4-(pentyloxy)benzylidene]-1,3-thiazol-4(5H)-one
93.3% inhibition at 0.01 mM
(5Z)-3-benzyl-5-[(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methylidene]-1,3-thiazolidine-2,4-dione
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(5Z)-5-(2-chlorobenzylidene)-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4(5H)-one
96.1% inhibition at 0.01 mM
(5Z)-5-(3,4-dichlorobenzylidene)-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4(5H)-one
(5Z)-5-(3,4-dichlorobenzylidene)-2-(piperazin-1-yl)-1,3-thiazol-4(5H)-one
(5Z)-5-(3,4-dichlorobenzylidene)-2-[4-[4-(dihydroxymethyl)benzyl]piperazin-1-yl]-1,3-thiazol-4(5H)-one
(5Z)-5-(3,4-dimethoxybenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1,3-thiazol-4(5H)-one
(5Z)-5-(3-bromobenzylidene)-2-(4-ethylpiperazin-1-yl)-1,3-thiazol-4(5H)-one
(5Z)-5-(4-chlorobenzylidene)-2-(4-ethylpiperazin-1-yl)-1,3-thiazol-4(5H)-one
(5Z)-5-(4-ethoxy-3-methoxybenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1,3-thiazol-4(5H)-one
(5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-(morpholin-4-yl)-1,3-thiazol-4(5H)-one
(5Z)-5-benzylidene-2-(4-ethylpiperazin-1-yl)-1,3-thiazol-4(5H)-one
1,10-phenanthroline
1,10-phenantroline
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50% inhibition at 2.5 mM, 70% inhibition
1-acyl glycerol 3-phosphate
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also fatty alcohol phosphates (structurally 1-acyl glycerol 3-phosphate analogs)
1-arachidonoyl-lysophosphatidic acid
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Clarification of the structural importance of acyl chain for the inhibitory effect of lysophosphatidic acid on lysoPLD activity. Lysophosphatidic acids with polyunsaturated acyl chains are more potent than those with saturated acyl chains in the inhibition of serum lysoPLD activity
1-arachidoyl-lysophosphatidic acid
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Clarification of the structural importance of acyl chain for the inhibitory effect of lysophosphatidic acid on lysoPLD activity. Lysophosphatidic acids with polyunsaturated acyl chains are more potent than those with saturated acyl chains in the inhibition of serum lysoPLD activity
1-bromo-3(s)-hydroxy-4-(palmitoyloxy) butylphosphonate
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inhibitory in vitro and in vivo
1-hexanoyl-lysophosphatidic acid
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Clarification of the structural importance of acyl chain for the inhibitory effect of lysophosphatidic acid on lysoPLD activity. Lysophosphatidic acids with polyunsaturated acyl chains are more potent than those with saturated acyl chains in the inhibition of serum lysoPLD activity
1-linoleoyl-lysophosphatidic acid
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Clarification of the structural importance of acyl chain for the inhibitory effect of lysophosphatidic acid on lysoPLD activity. Lysophosphatidic acids with polyunsaturated acyl chains are more potent than those with saturated acyl chains in the inhibition of serum lysoPLD activity
1-myristoyl-lysophosphatidic acid
1-oleoyl-lysophosphatidic acid
1-palmitoyl-lysophosphatidic acid
1-stearoyl-lysophosphatidic acid
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Clarification of the structural importance of acyl chain for the inhibitory effect of lysophosphatidic acid on lysoPLD activity. Lysophosphatidic acids with polyunsaturated acyl chains are more potent than those with saturated acyl chains in the inhibition of serum lysoPLD activity
2,2'-methylenebis(4-chlorophenol)
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2-(4-[[(2,3-dichlorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
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72.3% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(2,4,6-mesitylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
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53.5% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(2,5-dichlorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
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mixed inhibition, 5.4% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(2-benzothiadiazolphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
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63.2% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(2-chlorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
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83.5% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(2-fluorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
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77.3% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(2-iodophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
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68.4% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(2-methoxyphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
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97.6% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(2-methylesterphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
51.2% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(3,5-bis(trifluoromethyl)phenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
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competitive inhibition, 34.1% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(3,5-dimethylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
competitive inhibition, 30.4% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(3-benzothiadiazolphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
competitive inhibition, 28.6% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(3-chlorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
mixed inhibition, 9.7% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(3-fluorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
40.5% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(3-iodophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
mixed inhibition, 8.6% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(3-methoxyphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
40.9% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(3-methylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
competitive inhibition, 41.9% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(3-trifluoromethylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
competitive inhibition, 0.3% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(4-carboxylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
72.7% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(4-chlorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
competitive inhibition, 42.4% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(4-dimethylaminonapthylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
59.9% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(4-fluorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
48.9% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(4-iodophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
mixed inhibition, 32.7% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(4-methoxyphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
79.7% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(4-methylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
49.9% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(4-morpholinosulfonylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
64.1% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(4-pyrazolephenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
68.6% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(4-trifluoromethylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
noncompetitive inhibition, 36.2% residual activity at 0.001 mM using FS-3 as substrate
2-(4-[[(phenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid phenyl
-
56.4% residual activity at 0.001 mM using FS-3 as substrate
2-amino-2-(2-(4-octylphenyl) ethyl)propan-1,3-diol
-
synonyms FTY720, finolimod, competitive inhibition
2-carba cyclic phosphatidic acid
-
-
3-([4-[(Z)-(3-benzyl-2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-3-ethoxyphenoxy]methyl)benzoic acid
-
-
3-carba cyclic phosphatidic acid
-
-
3-[(4-[(Z)-[3-(4-fluorobenzyl)-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]-3-methoxyphenoxy)methyl]benzoic acid
-
competitive inhibition, 35% residual ATX activity at 0.005 mM
3-[(4-[(Z)-[3-(4-fluorobenzyl)-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenoxy)methyl]benzoic acid
-
competitive inhibition, 7% residual ATX activity at 0.005 mM
4-(5-[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]furan-2-yl)benzenesulfonamide
90.1% inhibition at 0.01 mM
4-amino-6-(2-[4'-[(E)-(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3,3'-dimethoxybiphenyl-4-yl]hydrazinyl)-5-hydroxynaphthalene-1,3-disulfonic acid
99.0% inhibition at 0.01 mM
4-amino-6-(2-{4'-[(E)-(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3,3'-dimethoxybiphenyl-4-yl}hydrazinyl)-5-hydroxynaphthalene-1,3-disulfonic acid
-
26.2% inhibition at 0.01 mM
4-chloro-N-methyl-N-{2-[2-(methylsulfonyl)hydrazinyl]-2-oxoethyl}benzenesulfonamide
70.7% inhibition at 0.01 mM
4-chloro-N-methyl-N-{2-[2-(methylsulfonyl)hydrazinyl]-2-oxoethyl}benzenesulfonamide (non-preferred name)
-
99.9% inhibition at 0.01 mM
4-[4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]butane-1-sulfonic acid
4-{5-[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]furan-2-yl}benzenesulfonamide
-
47.1% inhibition at 0.01 mM
5-[4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]pentanoic acid
ammonium chloride
-
-
ATP
-
extracellular enzyme
bis(para-nitrophenyl)phosphate
-
inhibition above a concentration of 1 mM
Bithionol
bovine serum albumin
-
concentration-dependent inhibition on lysoPLD activity in egg white during 24 h incubation
-
brefeldin-A
-
inhibitor of trans-Golgi transport, inhibits secretion of ATX
Ca2+
-
-
choline
-
-
cyclohexanaminium hydrogen [4-(decanoylamino)benzyl]phosphonate
-
-
cyclohexanaminium hydrogen [4-(heptanoylamino)benzyl]phosphonate
-
-
cyclohexanaminium hydrogen [4-(tetradecanoylamino)benzyl]phosphonate
-
-
cyclohexanaminium hydrogen [4-([3-[2-(2-methoxyethoxy)ethoxy]propanoyl]amino)benzyl]phosphonate
-
-
cyclohexanaminium hydrogen [fluoro[4-(heptanoylamino)phenyl]methyl]phosphonate
-
-
cyclohexanaminium hydrogen [[4-(decanoylamino)phenyl](fluoro)methyl]phosphonate
-
-
cyclohexanaminium hydrogen [[4-(decanoylamino)phenyl](hydroxy)methyl]phosphonate
-
-
cyclohexanaminium hydrogen [[4-(heptanoylamino)phenyl](hydroxy)methyl]phosphonate
-
-
D-histidine
-
15 mM, 75% inhibition
eosin Y
-
-
fatty alkyl phosphonate
-
-
fatty alkyl thiophosphate
-
-
FTY720-phosphate
-
-
FTY720P
-
binds apo-ATX and an ATX with bound FS-3/products complex, noncompetitive/mixed inhibition
G protein
-
G protein exhibits lysoPLD activity, lysoPLD activity is highly associated with heterotrimeric G protein
-
Globomycin
-
Treatment with the signal peptidase inhibitor inhibits ATX secretion by adipocytes treated for 6 h
H2L 5210574
-
mixed-mode inhibition against ATX-mediated FS-3 hydrolysis
H2L 5564949
-
mixed-mode inhibition against ATX-mediated FS-3 hydrolysis
H2L 5761473
-
competitive ATX inhibitor
H2L 7839888
-
mixed-mode inhibition against ATX-mediated FS-3 hydrolysis
H2L 7905958
H2L 7921385
-
non-competitive inhibitor
HA155
Hexachlorophene
-
-
histidine methylester
-
15 mM, 65% inhibition
histidineamide
-
15 mM, 20% inhibition
Human serum albumin
could be a regulator of the circulating autotaxin. When the albumin is a fatty acid-free preparation, this slight inhibition disappears; could be a regulator of the circulating autotaxin. When the albumin is a fatty acid-free preparation, this slight inhibition disappears
-
hypericin
iodoacetamide
-
-
isoquercitrin
-
-
isorhamnetin
-
-
isorhamnetin-3-O-glucoside
-
-
Ki16425
-
inhibits the migratory response of lysophosphatidic acid1-expressing cells to both lysophosphatidic acid and ATX
L-histidine
L-histidine amide
-
15 mM, 20% inhibition
L-histidine methylester
-
15 mM, 65% inhibition
lactacystin
-
proteasome inhibitor, restores the detection of ATX in cell homogenate of the mutants DELTAV12-V22 and DELTAV12-G27, Synthesis and secretion of ATX are highly dependent on the hydrophobic core of the signal peptide, but not on the amino acid composition the putative signal peptidase cleavage site
lysophosphatic acid
lysophosphatidic acid
lysozyme
-
concentration-dependent inhibition on lysoPLD activity in egg white during 24 h incubation
-
merbromin
-
-
murine serum albumin
could be a regulator of the circulating autotaxin. When the albumin is a fatty acid-free preparation, this slight inhibition disappears; could be a regulator of the circulating autotaxin. When the albumin is a fatty acid-free preparation, this slight inhibition disappears
-
myricetin
-
-
N-(2-chlorophenyl)-2-([(2E)-2-[1-(pyridin-2-yl)ethylidene]hydrazinyl]carbonothioyl)hydrazinecarbothioamide
N-ethylmaleimide
-
-
N-glycosidase
-
treatment with N-glycosidase inhibits lysophospholipase D activity of ATX. N-glycosylation of ATX strongly influences its secretion and its lysoPLD activity
-
N-methyl histidine
-
15 mM, 30% inhibition
N-methyl-L-histidine
-
15 mM, 30% inhibition
NaF
-
slight inhibition
NSC10881
-
-
NSC13792
-
-
NSC48300
-
-
NSC60016
-
-
NSC78785
-
-
NSC86629
-
-
oleoyl-LPA
-
inhibition of ATX pNP-TMP hydrolysis activity
p-hydroxymercuribenzoate
palmitoyl-lysophosphatidic acid
-
concentration-dependent inhibition of lysoPLD activity in egg white during 24 h incubation. More than 100 microM of lysophosphatidic acid needed to inhibit significantly lysoPLD activity of hen egg white
PF8380
quercetagetin
-
-
RJC 03297
-
-
robinetin
-
-
rutin
-
-
S32826
-
-
serine esterase inhibitors
-
inhibition of extracellular enzyme
-
sodium cholate
-
16 mM, 77% inhibition
sodium deoxycholate
-
6 mM, 100% inhibition
sphingosine 1-phosphate
sphingosine-1-phosphate
Triton X-100
-
0.3 mM, 64% inhibition
tunicamycin
-
inhibits secretion of ATX
[(2R,3S)-3-(hexadecanoylamino)-2-hydroxy-4-[4-(pyridin-2-ylmethoxy)phenyl]butyl]phosphonic acid
-
-
[(2R,3S)-3-(hexadecanoylamino)-2-hydroxy-4-[4-[(4-methoxy-3,5-dimethylbenzyl)oxy]phenyl]butyl]phosphonic acid
-
-
[(2R,3S)-3-(hexadecanoylamino)-2-hydroxy-4-[4-[(4-methoxy-3,5-dimethylpyridin-2-yl)methoxy]phenyl]butyl]phosphonic acid
-
i.e. VPC8a202
[(2R,3S)-3-(hexadecanoylamino)-2-hydroxy-4-[4-[(4-methoxy-3-methylbenzyl)oxy]phenyl]butyl]phosphonic acid
-
-
[(2R,3S)-3-(hexadecanoylamino)-2-hydroxy-4-[4-[(4-methoxypyridin-2-yl)methoxy]phenyl]butyl]phosphonic acid
-
-
[(2R,3S)-4-(4-[[3,5-dimethyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methoxy]phenyl)-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
-
-
[(2R,3S)-4-[4-(benzyloxy)phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
-
-
[(2R,3S)-4-[4-[(2,4-dichlorobenzyl)oxy]phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
-
-
[(2R,3S)-4-[4-[(3,5-dimethyl-4-propoxypyridin-2-yl)methoxy]phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
-
-
[(2R,3S)-4-[4-[(3,5-dimethylbenzyl)oxy]phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
-
-
[(2R,3S)-4-[4-[(3,5-dimethylpyridin-2-yl)methoxy]phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
-
-
[(2R,3S)-4-[4-[(4-ethoxy-3,5-dimethylpyridin-2-yl)methoxy]phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
-
-
[2-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid
[3-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid
[3-[(4-[(Z)-[3-(4-fluorobenzyl)-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenoxy)methyl]phenyl]boronic acid
-
mixed-type inhibition, complete inhibition at 0.005 mM
[4-(tetradecanoylamino)benzyl]phosphonic acid
[4-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
bFGF
-
induces a 1.9fold higher ATX mRNA expression
-
Co2+
-
extracellular enzyme
EGF
-
induces a 2.3fold higher ATX mRNA expression
-
heparin
IL-6
-
induces a marked increase in ATX mRNA expression
-
integrins
-
ATX activity against exogenously provided and cell-associated substrates is increased by integrin binding
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.097
1-alkyl-sn-glycero-3-phosphocholine
-
pH 7.4, 37C
0.1
1-alkyl-sn-glycero-3-phosphoethanolamine
-
achieved under optimal assay conditions, almost same results in blood plasma
0.0083
1-linoleoyl-2-lyso-glycerophoshorylcholine
-
Vmax is 0.019 micromol/min/mg
0.0267
1-O-hexadecyl-2-lyso-glycerophosphorylcholine
-
Vmax is 0.29 micromol/min/mg, lysoPLD activity is more than twice that observed with 1-palmitoyl-glycerophoshorylcholine
0.0207
1-palmitoyl-2-lyso-glycerophoshorylcholine
-
Vmax is 0.059 micromol/min/mg
0.176
1-palmitoyl-glycerophoshorylcholine
-
Vmax is 0.3 micromol/min/mg, best substrate
0.101
1-stearoyl-2-lyso-glycerophoshorylcholine
-
Vmax is 0.035 micromol/min/mg
0.7 - 5.6
4-nitrophenyl-TMP
0.0063
5-[[(23R)-33-(4-[[4-(dimethylamino)phenyl]diazenyl]phenyl)-20,23-dihydroxy-20-oxido-15,33-dioxo-3,6,9,12,19,21,25-heptaoxa-16,32-diaza-20-phosphatritriacont-1-yl]carbamoyl]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid
-
-
0.004
coumarin-phosphate-fluorescein
-
coumarin-phosphate-fluorescein is a fluorescence resonance energy transfer (FRET)-based sensor of phosphodiesterase activity. Very useful substrate for enzymatic analysis of purified autotaxin/lysoPLD and can also be used to detect autotaxin/lysoPLD activity in serum-free conditioned culture medium isolated from cells expressing the enzyme
0.0031
FS-2
-
-
0.0026 - 0.019
FS-3
0.094 - 0.66
lysophosphatidylcholine
0.066 - 0.126
lysophosphatidylcholine 16:0
0.089 - 0.27
lysophosphatidylcholine 18:0
0.069 - 0.126
lysophosphatidylcholine 18:1
0.004
[5-[[(23S)-33-(4-[(E)-[4-(dimethylamino)phenyl]diazenyl]phenyl)-20,23-dihydroxy-20-oxido-15,26,33-trioxo-3,6,9,12,19,21,25-heptaoxa-16,32-diaza-20-phosphatritriacont-1-yl]carbamoyl]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)phenyl]acetic acid
-
[5-[[(23S)-33-(4-[(E)-[4-(dimethylamino)phenyl]diazenyl]phenyl)-20,23-dihydroxy-20-oxido-15,26,33-trioxo-3,6,9,12,19,21,25-heptaoxa-16,32-diaza-20-phosphatritriacont-1-yl]carbamoyl]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)phenyl]acetic acid can be used to detect autotaxin/lysoPLD activity in human and mouse blood
additional information
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0001
1-acyl glycerol 3-phosphate
-
CPF4 FRET assay (change of fluorescence intensity), inihibition involves both a reduction in vmax and an increase in km, binding affinity is 1000fold stronger than to 1-alkyl-sn-glycero-3-phosphoethanolamine and analogue substrates
0.00055 - 0.0034
1-arachidonoyl-lysophosphatidic acid
0.01031 - 0.06
1-arachidoyl-lysophosphatidic acid
0.01299 - 0.06
1-hexanoyl-lysophosphatidic acid
0.00021 - 0.0018
1-linoleoyl-lysophosphatidic acid
0.005 - 0.0065
1-myristoyl-lysophosphatidic acid
0.0012 - 0.0096
1-oleoyl-lysophosphatidic acid
0.00141 - 0.0104
1-palmitoyl-lysophosphatidic acid
0.00209 - 0.0258
1-stearoyl-lysophosphatidic acid
0.0034
2-(4-[[(2,5-dichlorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.004
2-(4-[[(3,5-bis(trifluoromethyl)phenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0042
2-(4-[[(3,5-dimethylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0071
2-(4-[[(3-benzothiadiazolphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0026
2-(4-[[(3-chlorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0074
2-(4-[[(3-iodophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0045
2-(4-[[(3-methylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0007
2-(4-[[(3-trifluoromethylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0057
2-(4-[[(4-chlorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0132
2-(4-[[(4-iodophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0132
2-(4-[[(4-trifluoromethylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0002
2-amino-2-(2-(4-octylphenyl) ethyl)propan-1,3-diol
-
substrate p-nitrophenyl thymidine 5-monophosphate, pH 8.0, 30 min of incubation at 37C, measuring absorbance at 405 nm, twofold higher KI compared to inhibitor S1P
0.000018
cyclohexanaminium hydrogen [4-(decanoylamino)benzyl]phosphonate
-
pH and temperature not specified in the publication
0.000512
cyclohexanaminium hydrogen [4-(heptanoylamino)benzyl]phosphonate
-
pH and temperature not specified in the publication
0.000009
cyclohexanaminium hydrogen [4-(tetradecanoylamino)benzyl]phosphonate
-
pH and temperature not specified in the publication
0.000834
cyclohexanaminium hydrogen [fluoro[4-(heptanoylamino)phenyl]methyl]phosphonate
-
pH and temperature not specified in the publication
0.0000061 - 0.000072
cyclohexanaminium hydrogen [[4-(decanoylamino)phenyl](fluoro)methyl]phosphonate
0.000024 - 0.0000242
cyclohexanaminium hydrogen [[4-(decanoylamino)phenyl](hydroxy)methyl]phosphonate
0.001009
cyclohexanaminium hydrogen [[4-(heptanoylamino)phenyl](hydroxy)methyl]phosphonate
-
pH and temperature not specified in the publication
0.0151
H2L 5564949
-
with respect to ATX-mediated FS-3 hydrolysis
0.002
H2L 5761473
-
with respect to ATX-mediated FS-3 hydrolysis
0.0027
H2L 7839888
-
with respect to ATX-mediated FS-3 hydrolysis
0.0019 - 0.0065
H2L 7905958
0.0093
H2L 7921385
-
with respect to ATX-mediated FS-3 hydrolysis
0.00011
lysophosphatidic acid
-
-
0.00001
PF8380
-
pH and temperature not specified in the publication
0.00021 - 0.0018
sphingosine-1-phosphate
0.0225 - 0.027
[(2R,3S)-3-(hexadecanoylamino)-2-hydroxy-4-[4-(pyridin-2-ylmethoxy)phenyl]butyl]phosphonic acid
0.0047 - 0.2175
[(2R,3S)-3-(hexadecanoylamino)-2-hydroxy-4-[4-[(4-methoxy-3,5-dimethylbenzyl)oxy]phenyl]butyl]phosphonic acid
0.001 - 0.0111
[(2R,3S)-3-(hexadecanoylamino)-2-hydroxy-4-[4-[(4-methoxy-3,5-dimethylpyridin-2-yl)methoxy]phenyl]butyl]phosphonic acid
0.0088 - 0.0265
[(2R,3S)-3-(hexadecanoylamino)-2-hydroxy-4-[4-[(4-methoxy-3-methylbenzyl)oxy]phenyl]butyl]phosphonic acid
0.083
[(2R,3S)-3-(hexadecanoylamino)-2-hydroxy-4-[4-[(4-methoxypyridin-2-yl)methoxy]phenyl]butyl]phosphonic acid
-
anti configuration, pH and temperature not specified in the publication
0.0016 - 0.0035
[(2R,3S)-4-(4-[[3,5-dimethyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methoxy]phenyl)-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
0.0039 - 0.0116
[(2R,3S)-4-[4-(benzyloxy)phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
0.0889 - 0.399
[(2R,3S)-4-[4-[(2,4-dichlorobenzyl)oxy]phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
0.0015 - 1.059
[(2R,3S)-4-[4-[(3,5-dimethyl-4-propoxypyridin-2-yl)methoxy]phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
0.0043 - 0.0062
[(2R,3S)-4-[4-[(3,5-dimethylbenzyl)oxy]phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
0.0044
[(2R,3S)-4-[4-[(3,5-dimethylpyridin-2-yl)methoxy]phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
-
syn configuration, pH and temperature not specified in the publication
0.011 - 0.5841
[(2R,3S)-4-[4-[(4-ethoxy-3,5-dimethylpyridin-2-yl)methoxy]phenyl]-3-(hexadecanoylamino)-2-hydroxybutyl]phosphonic acid
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00011
(5Z)-3-benzyl-5-[(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methylidene]-1,3-thiazolidine-2,4-dione
Mus musculus
-
in Tris-HCl buffer (pH 7.4) at 37C
0.00017
(5Z)-5-(3,4-dichlorobenzylidene)-2-(piperazin-1-yl)-1,3-thiazol-4(5H)-one
Mus musculus
Q9R1E6
pH 9.0, 37C
0.000025
(5Z)-5-(3,4-dichlorobenzylidene)-2-[4-[4-(dihydroxymethyl)benzyl]piperazin-1-yl]-1,3-thiazol-4(5H)-one
Mus musculus
Q9R1E6
pH 9.0, 37C
0.0013
2-(4-[[(2,5-dichlorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0341
2-(4-[[(3,5-bis(trifluoromethyl)phenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0304
2-(4-[[(3,5-dimethylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0286
2-(4-[[(3-benzothiadiazolphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0097
2-(4-[[(3-chlorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0161
2-(4-[[(3-fluorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0016
2-(4-[[(3-iodophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0177
2-(4-[[(3-methoxyphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0135
2-(4-[[(3-methylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0009
2-(4-[[(3-trifluoromethylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0107
2-(4-[[(4-chlorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0177
2-(4-[[(4-fluorophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0015
2-(4-[[(4-iodophenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0161
2-(4-[[(4-methylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0327
2-(4-[[(4-trifluoromethylphenyl)amino]carbonothioyl]-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid
Homo sapiens
-
1 mM each CaCl2 and MgCl2, 5 mM KCl, and 140 mM NaCl, in 50 mM Tris, pH 8.0, at 37C
0.0003
2-amino-2-(2-(4-octylphenyl) ethyl)propan-1,3-diol
Homo sapiens
-
to 0.0004, substrate p-nitrophenyl thymidine 5-monophosphate, pH 8.0, 30 min of incubation at 37C, measuring absorbance at 405 nm, compared to inhibitor S1P 0.0001 mM
0.000161
3-([4-[(Z)-(3-benzyl-2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-3-ethoxyphenoxy]methyl)benzoic acid
Mus musculus
-
in Tris-HCl buffer (pH 7.4) at 37C
0.0025
3-[(4-[(Z)-[3-(4-fluorobenzyl)-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]-3-methoxyphenoxy)methyl]benzoic acid
Mus musculus
-
in Tris-HCl buffer (pH 7.4) at 37C
0.0017
3-[(4-[(Z)-[3-(4-fluorobenzyl)-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenoxy)methyl]benzoic acid
Mus musculus
-
in Tris-HCl buffer (pH 7.4) at 37C
0.00023
4-[4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]butane-1-sulfonic acid
Mus musculus
Q9R1E6
pH 9.0, 37C
0.00039
5-[4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]pentanoic acid
Mus musculus
Q9R1E6
pH 9.0, 37C
0.0068
H2L 5210574
Homo sapiens
-
with respect to ATX-mediated 4-nitrophenyl-TMP hydrolysis; with respect to ATX-mediated FS-3 hydrolysis
0.0128
H2L 5564949
Homo sapiens
-
with respect to ATX-mediated FS-3 hydrolysis
0.0128
H2L 5761473
Homo sapiens
-
with respect to ATX-mediated FS-3 hydrolysis
0.0015 - 0.0017
H2L 7839888
0.0012 - 0.0016
H2L 7905958
0.0016
H2L 7921385
Homo sapiens
-
with respect to ATX-mediated FS-3 hydrolysis
0.0753 - 0.1035
Human serum albumin
-
0.0016 - 0.0029
hypericin
0.000016 - 0.000038
lysophosphatidic acid
0.187 - 0.317
murine serum albumin
-
0.00058
[2-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid
Mus musculus
Q9R1E6
pH 9.0, 37C
0.000013
[3-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid
Mus musculus
Q9R1E6
pH 9.0, 37C
0.000028
[3-[(4-[(Z)-[3-(4-fluorobenzyl)-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenoxy)methyl]phenyl]boronic acid
Mus musculus
-
in Tris-HCl buffer (pH 7.4) at 37C
0.000022
[4-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid
Mus musculus
Q9R1E6
pH 9.0, 37C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000005 - 0.000076
-
depending on presence of divalent cations
0.00009
-
lung
0.0002
-
testis
0.00022
-
liver
0.00034
-
kidney
0.00037
-
intestine
0.0051
Murine autotaxin gamma, p-nitrophenyl phenylphosphonate as a substrate, Vmax 1.8 nmol p-nitrophenyl/min
0.00847
human autotaxin alpha, p-nitrophenyl phenylphosphonate as a substrate, Vmax 0.67 nmol p-nitrophenyl/min
0.0163
Murine autotaxin alpha, p-nitrophenyl phenylphosphonate as a substrate, Vmax 0.35 nanomol p-nitrophenyl/min
0.036
-
using isotopic assay
0.048
-
colorimetric assay, 6 h incubation, 37C
0.0919
Murine autotaxin beta, para-nitrophenyl phenylphosphonate as a substrate, Vmax 1.9 nmol para-nitrophenyl/min
0.0997
Human autotaxin gamma, p-nitrophenyl phenylphosphonate as a substrate, Vmax 1.6 nmol p-nitrophenyl/min
0.135
Human autotaxin beta, p-nitrophenyl phenylphosphonate as a substrate, Vmax 1.9 nmol p-nitrophenyl/min
0.14
-
purified enzyme, HiTrap DEAE FF
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 7.5
-
highest enzyme activity
7
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 9.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
38.5
-
assay at
45 - 55
murine isoform beta maximally active at 4555C; murine isoform gamma is maximally active at 4555C
45 - 60
purified isoforms show temperature dependence; purified isoforms show temperature dependence. beta isoform plateaus from 45 to 60C, alpha isoform remains not much sensitive to temperature and little active
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 60
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
secrets the mature ATX
Manually annotated by BRENDA team
-
the enzyme is constitutively released from corneal tissues and/or ciliary body into the aqueous humor, with no injury-induced increase in release following freeze-wounding
Manually annotated by BRENDA team
-
corneal stromal cells and endothelial and epithelial cells, the enzyme is constitutively released from corneal tissues and/or ciliary body into the aqueous humor, with no injury-induced increase in release following freeze-wounding
Manually annotated by BRENDA team
-
embryonic spinal cord
Manually annotated by BRENDA team
-
LysoPLD activity is determined in culture medium from control cells or cells expressing V5-autotaxin (ATX)
Manually annotated by BRENDA team
-
Various concentrations of hATX S48 protein are exposed to HT-1080 cells and motile area is analyzed. hATX S48 protein also affects cell proliferation
Manually annotated by BRENDA team
-
cancer cell line
Manually annotated by BRENDA team
-
Detection of lysophospholipase D/autotoxin (lysoPLD/ATX) antigen in the urine samples of patients with nephrotic syndrome, both with active and inactive disease states. LysoPLD/ATX antigen detection in the urine and its concentrations seem to be correlated with the total urinary protein concentrations
Manually annotated by BRENDA team