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Literature summary extracted from

  • Kawaguchi, M.; Okabe, T.; Okudaira, S.; Nishimasu, H.; Ishitani, R.; Kojima, H.; Nureki, O.; Aoki, J.; Nagano, T.
    Screening and X-ray crystal structure-based optimization of autotaxin (ENPP2) inhibitors, using a newly developed fluorescence probe (2013), ACS Chem. Biol., 8, 1713-1721.
    View publication on PubMed

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
3.1.4.39 crystal structure determination and analysis of enzyme in complexes with inhibitors 2BoA, 3BoA, and 4BoA, at 1.95 A, 1.90 A, and 1.75 A resolution Mus musculus

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.1.4.39 (5Z)-2-(4-ethylpiperazin-1-yl)-5-(4-fluorobenzylidene)-1,3-thiazol-4(5H)-one 93.8% inhibition at 0.01 mM Mus musculus
3.1.4.39 (5Z)-2-(azepan-1-yl)-5-(4-propoxybenzylidene)-1,3-thiazol-4(5H)-one 96.6% inhibition at 0.01 mM Mus musculus
3.1.4.39 (5Z)-2-(morpholin-4-yl)-5-[4-(pentyloxy)benzylidene]-1,3-thiazol-4(5H)-one 93.3% inhibition at 0.01 mM Mus musculus
3.1.4.39 (5Z)-5-(2-chlorobenzylidene)-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4(5H)-one 96.1% inhibition at 0.01 mM Mus musculus
3.1.4.39 (5Z)-5-(3,4-dichlorobenzylidene)-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4(5H)-one 10.5% inhibition at 0.01 mM Danio rerio
3.1.4.39 (5Z)-5-(3,4-dichlorobenzylidene)-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4(5H)-one 94.9% inhibition at 0.01 mM Mus musculus
3.1.4.39 (5Z)-5-(3,4-dichlorobenzylidene)-2-(piperazin-1-yl)-1,3-thiazol-4(5H)-one
-
 Danio rerio
3.1.4.39 (5Z)-5-(3,4-dichlorobenzylidene)-2-(piperazin-1-yl)-1,3-thiazol-4(5H)-one
-
 Mus musculus
3.1.4.39 (5Z)-5-(3,4-dichlorobenzylidene)-2-[4-[4-(dihydroxymethyl)benzyl]piperazin-1-yl]-1,3-thiazol-4(5H)-one
-
 Danio rerio
3.1.4.39 (5Z)-5-(3,4-dichlorobenzylidene)-2-[4-[4-(dihydroxymethyl)benzyl]piperazin-1-yl]-1,3-thiazol-4(5H)-one
-
 Mus musculus
3.1.4.39 (5Z)-5-(3,4-dimethoxybenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1,3-thiazol-4(5H)-one 18.1% inhibition at 0.01 mM Danio rerio
3.1.4.39 (5Z)-5-(3,4-dimethoxybenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1,3-thiazol-4(5H)-one 95.3% inhibition at 0.01 mM Mus musculus
3.1.4.39 (5Z)-5-(3-bromobenzylidene)-2-(4-ethylpiperazin-1-yl)-1,3-thiazol-4(5H)-one 70.9% inhibition at 0.01 mM Danio rerio
3.1.4.39 (5Z)-5-(3-bromobenzylidene)-2-(4-ethylpiperazin-1-yl)-1,3-thiazol-4(5H)-one 90.7% inhibition at 0.01 mM Mus musculus
3.1.4.39 (5Z)-5-(4-chlorobenzylidene)-2-(4-ethylpiperazin-1-yl)-1,3-thiazol-4(5H)-one 6.2% inhibition at 0.01 mM Danio rerio
3.1.4.39 (5Z)-5-(4-chlorobenzylidene)-2-(4-ethylpiperazin-1-yl)-1,3-thiazol-4(5H)-one 91.5% inhibition at 0.01 mM Mus musculus
3.1.4.39 (5Z)-5-(4-ethoxy-3-methoxybenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1,3-thiazol-4(5H)-one 15.7% inhibition at 0.01 mM Danio rerio
3.1.4.39 (5Z)-5-(4-ethoxy-3-methoxybenzylidene)-2-[4-(2-hydroxyethyl)piperazin-1-yl]-1,3-thiazol-4(5H)-one 92.2% inhibition at 0.01 mM Mus musculus
3.1.4.39 (5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-(morpholin-4-yl)-1,3-thiazol-4(5H)-one 23.7% inhibition at 0.01 mM Danio rerio
3.1.4.39 (5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-(morpholin-4-yl)-1,3-thiazol-4(5H)-one 93.2% inhibition at 0.01 mM Mus musculus
3.1.4.39 (5Z)-5-benzylidene-2-(4-ethylpiperazin-1-yl)-1,3-thiazol-4(5H)-one 69.4% inhibition at 0.01 mM Danio rerio
3.1.4.39 (5Z)-5-benzylidene-2-(4-ethylpiperazin-1-yl)-1,3-thiazol-4(5H)-one 97.7% inhibition at 0.01 mM Mus musculus
3.1.4.39 4-(5-[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]furan-2-yl)benzenesulfonamide 90.1% inhibition at 0.01 mM Mus musculus
3.1.4.39 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 Mus musculus
3.1.4.39 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 Danio rerio
3.1.4.39 4-chloro-N-methyl-N-{2-[2-(methylsulfonyl)hydrazinyl]-2-oxoethyl}benzenesulfonamide 70.7% inhibition at 0.01 mM Mus musculus
3.1.4.39 4-chloro-N-methyl-N-{2-[2-(methylsulfonyl)hydrazinyl]-2-oxoethyl}benzenesulfonamide (non-preferred name) 99.9% inhibition at 0.01 mM Danio rerio
3.1.4.39 4-[4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]butane-1-sulfonic acid
-
 Danio rerio
3.1.4.39 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
3.1.4.39 4-{5-[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]furan-2-yl}benzenesulfonamide 47.1% inhibition at 0.01 mM Danio rerio
3.1.4.39 5-[4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]pentanoic acid
-
 Danio rerio
3.1.4.39 5-[4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]pentanoic acid
-
 Mus musculus
3.1.4.39 HA155
-
 Danio rerio
3.1.4.39 HA155
-
 Mus musculus
3.1.4.39 additional information inhibitor screening of thiazolone derivatives, overview. Screening for specific enzyme inhibitors using TG-mTMP, a highly sensitive fluorescence probe for the enzyme, that consists of enzyme recognition moiety, linker moiety, and fluorophore. It is almost nonfluorescent before the enzymatic reaction, and the enzyme generates strongly fluorescent 6-hydroxy-9-(4-methoxy-2-methylphenyl)-3H-xanthen-3-one with elimination of thymidine monophosphate and formaldehyde. In vitro and In vivo studies and evaluation of optimized inhibitors. No or poor inhibition by (5Z)-2-(azepan-1-yl)-5-(4-propoxybenzylidene)-1,3-thiazol-4(5H)-one, (5Z)-2-(morpholin-4-yl)-5-[4-(pentyloxy)benzylidene]-1,3-thiazol-4(5H)-one, (5Z)-2-(4-ethylpiperazin-1-yl)-5-(4-fluorobenzylidene)-1,3-thiazol-4(5H)-one, and (5Z)-5-(2-chlorobenzylidene)-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4(5H)-one Danio rerio
3.1.4.39 additional information inhibitor screening of thiazolone derivatives, overview. Screening for specific enzyme inhibitors using TG-mTMP, a highly sensitive fluorescence probe for the enzyme, that consists of enzyme recognition moiety, linker moiety, and fluorophore. It is almost nonfluorescent before the enzymatic reaction, and the enzyme generates strongly fluorescent 6-hydroxy-9-(4-methoxy-2-methylphenyl)-3H-xanthen-3-one with elimination of thymidine monophosphate and formaldehyde. In vitro and In vivo studies and evaluation of optimized inhibitors, inhibitory potencies of monosubstituted and disubstituted aryl-methyl derivatives, overview Mus musculus
3.1.4.39 N-(2-chlorophenyl)-2-([(2E)-2-[1-(pyridin-2-yl)ethylidene]hydrazinyl]carbonothioyl)hydrazinecarbothioamide 58.3% inhibition at 0.01 mM Danio rerio
3.1.4.39 N-(2-chlorophenyl)-2-([(2E)-2-[1-(pyridin-2-yl)ethylidene]hydrazinyl]carbonothioyl)hydrazinecarbothioamide 71.5% inhibition at 0.01 mM Mus musculus
3.1.4.39 PF8380
-
 Danio rerio
3.1.4.39 PF8380
-
 Mus musculus
3.1.4.39 [2-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid binding structure, overview Danio rerio
3.1.4.39 [2-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid binding structure, overview Mus musculus
3.1.4.39 [3-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid binding structure, overview Danio rerio
3.1.4.39 [3-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid binding structure, overview Mus musculus
3.1.4.39 [4-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid binding structure, overview Danio rerio
3.1.4.39 [4-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid binding structure, overview Mus musculus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
3.1.4.39 extracellular
-
 Mus musculus
-
-

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
3.1.4.39 Mg2+ required Danio rerio
3.1.4.39 Mg2+ required Mus musculus
3.1.4.39 Zn2+ enzyme-bound, required Danio rerio
3.1.4.39 Zn2+ enzyme-bound, required Mus musculus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.1.4.39 additional information Danio rerio the enzyme converts lysophospholipids such as lysophosphatidylcholine to lysophosphatidic acid ?
-
 ?
3.1.4.39 additional information Mus musculus the enzyme converts lysophospholipids such as lysophosphatidylcholine to lysophosphatidic acid ?
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.1.4.39 Danio rerio
-
-
-
3.1.4.39 Mus musculus Q9R1E6
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.1.4.39 breast cancer cell
-
 Mus musculus
-
3.1.4.39 breast cancer cell overexpression of the enzyme is frequently observed in cancer tissues, such as breast cancer and glioblastoma Mus musculus
-
3.1.4.39 glioblastoma cell
-
 Mus musculus
-
3.1.4.39 plasma
-
 Mus musculus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.4.39 additional information the enzyme converts lysophospholipids such as lysophosphatidylcholine to lysophosphatidic acid Danio rerio ?
-
 ?
3.1.4.39 additional information the enzyme converts lysophospholipids such as lysophosphatidylcholine to lysophosphatidic acid Mus musculus ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.1.4.39 ATX
-
 Danio rerio
3.1.4.39 ATX
-
 Mus musculus
3.1.4.39 lysophospholipase D
-
 Danio rerio
3.1.4.39 lysophospholipase D
-
 Mus musculus
3.1.4.39 lysoPLD
-
 Danio rerio
3.1.4.39 lysoPLD
-
 Mus musculus
3.1.4.39 mATX
-
 Mus musculus
3.1.4.39 zATX
-
 Danio rerio

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.1.4.39 37
-
 assay at Danio rerio
3.1.4.39 37
-
 assay at Mus musculus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.1.4.39 9
-
 assay at Danio rerio
3.1.4.39 9
-
 assay at Mus musculus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.1.4.39 0.000013
-
 pH 9.0, 37°C Mus musculus [3-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid
3.1.4.39 0.000022
-
 pH 9.0, 37°C Mus musculus [4-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid
3.1.4.39 0.000025
-
 pH 9.0, 37°C Mus musculus (5Z)-5-(3,4-dichlorobenzylidene)-2-[4-[4-(dihydroxymethyl)benzyl]piperazin-1-yl]-1,3-thiazol-4(5H)-one
3.1.4.39 0.00017
-
 pH 9.0, 37°C Mus musculus (5Z)-5-(3,4-dichlorobenzylidene)-2-(piperazin-1-yl)-1,3-thiazol-4(5H)-one
3.1.4.39 0.00023
-
 pH 9.0, 37°C Mus musculus 4-[4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]butane-1-sulfonic acid
3.1.4.39 0.00039
-
 pH 9.0, 37°C Mus musculus 5-[4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]pentanoic acid
3.1.4.39 0.00058
-
 pH 9.0, 37°C Mus musculus [2-([4-[(5Z)-5-(3,4-dichlorobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]piperazin-1-yl]methyl)phenyl]boronic acid

General Information

EC Number General Information Comment Organism
3.1.4.39 evolution mouse and human enzymes show high structural homology Mus musculus
3.1.4.39 physiological function the enzyme is the predominant contributor to lysophosphatidic acid production in the human body, especially in the blood, and therefore has important roles in various physiological functions, including development of vasculature and lymphocyte trafficking Mus musculus