Information on EC 5.3.99.5 - Thromboxane-A synthase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY hide
5.3.99.5
-
RECOMMENDED NAME
GeneOntology No.
Thromboxane-A synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate = (5Z,13E)-(15S)-9alpha,11alpha-epoxy-15-hydroxythromboxa-5,13-dienoate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
intramolecular oxidoreduction
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isomerization
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Arachidonic acid metabolism
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C20 prostanoid biosynthesis
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate isomerase
A cytochrome P-450 heme-thiolate enzyme. Converts prostaglandin H2 into thromboxane A2.
CAS REGISTRY NUMBER
COMMENTARY hide
61276-89-9
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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
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9a,11a-epoxy-15-hydroxythromboxa-5,13-dienoate
show the reaction diagram
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i.e. TXA2
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,11alpha-epoxy-15-hydroxythromboxa-5,13-dienoate
show the reaction diagram
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
12-L-hydroxy-5,8,10-heptadecaotrienoic acid + malondialdehyde
show the reaction diagram
15-hydroperoxyeicosatetraenoic acid
13-hydroxy-14,15-epoxy-5,8,11-eicosatrienoic acid + 15-ketoeicosatetraenoic acid + 13-hydroxy-14,15-epoxy-5,8,11-eicosatrienoic acid + 15-ketoeicosatetraenoic acid
show the reaction diagram
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13-hydroxy-14,15-epoxy-5,8,11-eicosatrienoic acid and 15-ketoeicosatetraenoic acid result from homolytic cleavage of the O-O bond, whereas 13-hydroxy-14,15-epoxy-5,8,11-eicosatrienoic acid + 15-ketoeicosatetraenoic acid results from heterolytic cleavage. About 60% of substrate is cleaved homolytically, and maximal velocity of homolytic cleavage is about 1.4fold faster than heterolytic cleavage
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?
15-Ketoprostaglandin H2
?
show the reaction diagram
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8-Isoprostaglandin H2
8-cis-12-Hydroperoxy-5,8,10-heptadecatrienoic acid
show the reaction diagram
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prostaglandin E2
thromboxane A2 + ?
show the reaction diagram
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thromoboxane A2 is non-enzymatically converted to thromboxane B2, which is secretion is measured to analyze the enzyme activity
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?
prostaglandin G2
15-hydroperoxythromboxane A2 + 12-hydroperoxy-5,8,10-heptadecatrienoic acid
show the reaction diagram
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i.e. PGG2
the reaction products are transformed to thromboxane B2 and 12-hydroxy-5,8,10-heptadecatrienoic acid by SnCl2 reduction and to 12-keto-5,8,10-heptadecatrienoic acid and 15-ketothromboxane B2 by lead tetraacetate dehydration
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Prostaglandin G2
15-Hydroperoxythromboxane B2 + 12-hydroperoxy-5,8,10-heptadecatrienoic acid
show the reaction diagram
prostaglandin H1
12(L)-hydroxy-8,10-heptadecadienoic acid + thromboxane B1
show the reaction diagram
prostaglandin H2
thromboxane A2 + ?
show the reaction diagram
Prostaglandin H2
Thromboxane B2 + 12(L)-hydroxy-5,8,10-heptadecatrienoic acid
show the reaction diagram
prostaglandin H2
thromboxane B2 + 12(S)-hydroxy-5,8,10-heptadecatrienoic acid
show the reaction diagram
Prostaglandin H3
Thromboxane B3 + 12(L)-hydroxy-5,8,10,14-heptadecatetraenoic acid
show the reaction diagram
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the ratio of thromboxane to C17 hydroxyfatty acid formation is 1:1. Thromboxane A2 is fully transformed to thromboxane B2
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Prostaglandin H3
Thromboxane B3 + DELTA14-12-hydroperoxy-5,8,10-heptadecatrienoic acid
show the reaction diagram
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15(S)-Hydroxy-11alpha,9alpha-epoxymethano-5(Z),13(E)-prostadienoic acid
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
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,11alpha-epoxy-15-hydroxythromboxa-5,13-dienoate
show the reaction diagram
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
12-L-hydroxy-5,8,10-heptadecaotrienoic acid + malondialdehyde
show the reaction diagram
prostaglandin H2
thromboxane A2 + ?
show the reaction diagram
prostaglandin H2
thromboxane B2 + 12(S)-hydroxy-5,8,10-heptadecatrienoic acid
show the reaction diagram
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?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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cyanide binding to substrate-free and substrate-bound CYP5A1 in a detergent-solubilized system and in nanodiscs, binding kinetics, overview
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-(E)-7-[4-[4-[[[2-(trans)-phenylcyclopropyl]amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000085 mM, 50% inhibition
(+)-5-(2-imidazole-1-ethyloxy)-1-indan-carboxylic acid
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trivial name camonagrel
(+/-)-6-(1-Imidazolylmethyl)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid hydrochloride hemihydrate
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improvement of the renal function with the selective thromboxane A2 synthetase inhibitor
(-)-(E)-7-[4-[4-[[[2-(trans)-phenylcyclopropyl]amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000059 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3,3-dimethyl)guanidinophenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.000026 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-(1-adamantyl)-guanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.000003 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-(2-dimethylaminoethyl)-guanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.0029 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-(2-methylpropyl)guanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.000025 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-(3-methylbutyl)guanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.000003 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-(3-pyridylmethyl)-guanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.000032 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-benzylguanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.000011 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-cyclohexyl-guanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.000003 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-cyclopentyl-guanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.000003 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-cyclopropyl-guanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.00038 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-isopropyl)guanidinophenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.000024 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-methyl)guanidinophenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.00025 mM, 50% inhibition
(5E)-6-(3-(2-cyano-3-tert-butyl-guanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.000004 mM, 50% inhibition
(5E)-6-(4-(2-cyano-3-cyclopentyl-guanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.00018 mM, 50% inhibition
(5E)-6-(4-(2-cyano-3-cyclopropyl-guanidino)phenyl)-6-(3-pyridyl)hex-5-enoic acid
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0.0039 mM, 50% inhibition
(5Z)-6-[(2S,4R)-4-(4-Chlorophenylsulphonylamino)-1-(3-pyridylmethyl)-2-pyrrolidinyl]-5-hexenoic acid hydrochloride
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thromboxane A2 synthetase inhibitor/thromboxane A2-receptor antagonist
(E)-3-[4-(1-Imidazolylmethyl)phenyl]-2-propenoate
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reversible
(E)-6-[4-(3-tert-butyl-2-cyanoguanidino)phenyl]-6-(3-pyridyl)hex-5-enoic acid
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trivial name terbogrel
(E)-7-[4-[4-[(benzylamino)carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.000025 mM, 50% inhibition
(E)-7-[4-[4-[(pentylamino)carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridiyl)hept-6-enoic acid
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0.000031 mM, 50% inhibition
(E)-7-[4-[4-[(phenylethylamino)carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000094 mM, 50% inhibition
(E)-7-[4-[4-[[(2-phenoxybutyl)amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.000049 mM, 50% inhibition
(E)-7-[4-[4-[[(2-phenoxyethyl)amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000026 mM, 50% inhibition
(E)-7-[4-[4-[[(2-phenoxypentyl)amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.000049 mM, 50% inhibition
(E)-7-[4-[4-[[(4-cyclohexylbutyl)amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.000055 mM, 50% inhibition
(E)-7-[4-[4-[[(4-cyclopropylmethyl)amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.000025 mM, 50% inhibition
(E)-7-[4-[4-[[3-(morpholinopropyl)amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000051 mM, 50% inhibition
(E)-7-[4-[4-[[[2-(benzyloxy)ethyl]amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.000048 mM, 50% inhibition
(E)-7-[4-[4-[[[2-(cyclohexylmethoxy)ethyl]amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000037 mM, 50% inhibition
(E)-7-[4-[4-[[[2-(cyclohexyloxy)ethyl]amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000033 mM, 50% inhibition
(E)-7-[4-[4-[[[2-(tetrahydropyran-2-ylmethoxy)ethyl]amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000063 mM, 50% inhibition
(E)-7-[4-[4-[[[3-(1-cyclohexylethoxy)propyl]amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000012 mM, 50% inhibition
(E)-7-[4-[4-[[[3-(4-methoxyphenyl)propyl]amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000027 mM, 50% inhibition
(E)-7-[4-[4-[[[3-(cyclohexyloxy)propyl]amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000042 mM, 50% inhibition
(E)-7-[4-[4-[[[3-[(cis)-4-methoxycyclohexyl]propyl]amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000029 mM, 50% inhibition
(E)-7-[4-[4-[[[4-(cyclohexyloxy)butyl]amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid
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0.0000049 mM, 50% inhibition
([5-[2-([[(1E)-phenyl(pyridin-3-yl)methylidene]amino]oxy)ethyl]-7,8-dihydronaphthalen-1-yl]oxy)acetic acid
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i.e. ONO-1301, in addition to inhibitory activity, application of ONO-1301 significantly attenuates the development of pulmonary fibrosis and improves survival after treatment with bleomycin
1(omega-Carboxylalkyl)imidazoles
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very potent
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1-(2-Isopropylphenyl)-imidazole
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strong
1-Benzylimidazole
1-Decylimidazole
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strong
1-Methyl imidazole
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1-Nonylimidazole
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strong
1-[2-(4,5,6,7-tetrahydrobenzo[b]furan-4-yl)ethyl]-1H-imidazole
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0.001 mM, 50% inhibition
1-[2-(4,5,6,7-tetrahydrobenzo[b]furan-4-ylidene)ethyl]-1H-imidazole
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E isomer, 0.00355 mM, 50% inhibition; Z isomer, 0.0041 mM, 50% inhibition
1-[2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)ethyl]-1H-imidazole
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0.0012 mM, 50% inhibition
1-[2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-ylidene)ethyl]-1H-imidazole
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E isomer, 0.0017 mM, 50% inhibition; Z isomer, 0.0013 mM, 50% inhibition
1-[2-(benzo[b]thiophen-4-yl)ethyl]-1H-imidazole
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0.0053 mM, 50% inhibition
1-[3-(4-Benzylhydryl-1-piperazinyl)propyl]-3-(1H-imidazol-1-ylmethyl)-1H-indole-6-carboxylic acid
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strong thromboxane synthetase inhibition and H1-blocking activity
12L-Hydroperoxy-5,8,10,14-eicosatetraenoic acid
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0.1 mM, 50% inhibition
15-hydroperoxyeicosatetraenoic acid
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15-Hydroxy-11alpha,9alpha-(epoxymethano)-prosta-5,13-dienoic acid
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reversible
15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoic acid
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irreversible inactivation during catalysis, protection by (E)-3-[4-(1-imidazolylmethyl)phenyl]-2-propenoate and 15-hydroxy-11alpha,9alpha-(epoxymethano)-prosta-5,13-dienoic acid
1H-Imidazol-1-ylalyl-substituted 3-[2-[(arylsulfonyl)amino]ethyl]benzenepropanoic acid derivatives
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dual thromboxane synthase inhibitor/thromboxane receptor antagonists
2-Isopropyl-3-nicotinylindole
2-[4-Carboxy-8-(5-imidazol[1,5-a]pyridinyl)octanoyl]-2,3-dihydro-1H-1-isoindole-1-carboxylic acid
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2-[[1-(Carboxymethyl)-2,3,4,5,-tetrahydro-2-oxo-1H-1-benzazepin-3-yl]amino]-6-[[5-[5-chloro-1-methyl-2-(3-pyridinyl)-1H-indol-3-yl]pentanoyl]amino]hexanoic acid
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2-[[1-(Carboxymethyl)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3-yl]amino]6-[[5-[5-chloro-1-methyl-2-(3-pyridinyl)-1H-indol-3-yl]pentanoyl](2-hydroxyethyl)amino]hexanoic acid
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2-[[1-(Carboxymethyl)-2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3-yl]amino]-6-[[1-[5-[5-chloro-1-methyl-2-(3-pyridinyl)1H-indol-3-yl]pentanoyl]piperidin-4-yl]amino]hexanoic acid
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2-[[1-(Carboxymethyl)-2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3-yl]amino]-6-[[5-[5-chloro-1-methyl-2-(3-pyridinyl)1H-indol-3-yl]pentanoyl][2-(methylamino)ethyl]amino]hexanoic acid
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2-[[1-(Carboxymethyl)-2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3-yl]amino]-7-[[2-[[5-[5-chloro-1-methyl-2-(3-pyridinyl)1H-indol-3-yl]pentanoyl]amino]ethyl]amino]heptanoic acid
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3-Pyridinylalkyl-substituted 3-[2-[(arylsulfonyl)amino]ethyl]benzenepropanoic acid derivatives
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dual thromboxane synthase inhibitor/thromboxane receptor antagonists
4-(4-fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)imidazole
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trivial name SB203580
4-(Benzylamino)-2-(3'-pyridyl)quinazoline
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-
4-(Benzylamino)-2-(imidazol-1-yl)-quinazoline
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-
5-[2-(imidazol-1-yl)-ethyl]-5,6,7,8-tetrahydroquinoline
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0.00063 mM, 50% inhibition
5-[2-(imidazol-1-yl)ethyl]-1,2,3,4-tetrahydronaphthalene
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0.0034 mM, 50% inhibition
5-[2-(imidazol-1-yl)ethyl]-7,8-dihydroquinoline
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0.00029 mM, 50% inhibition
5-[2-(imidazol-1-yl)ethyl]quinoline
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0.0012 mM, 50% inhibition
5-[3-(imidazol-1-yl)-propyl]-5,6,7,8-tetrahydroquinoline
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0.0023 mM, 50% inhibition
5-[3-(imidazol-1-yl)-propyl]-7,8-dihydroquinoline
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0.00068 mM, 50% inhibition
5-[imidazol-1-yl-methyl]-5,6,7,8-tetrahydroquinoline
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0.002 mM, 50% inhibition
5-[imidazol-1-yl-methyl]-7,8-dihydroquinoline
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0.0015 mM, 50% inhibition
5E-6-(3-cyanoguanidino)phenyl-6-(3-pyridyl)hex-5-enoic acid
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0.00043 mM, 50% inhibition
5Z-6[(2S,4R)-4-(4-Chlorophenylsulfonylamino)-1-(3-pyridylmethyl)-2-pyrrolidinyl]-5-hexenoic acid
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causes marked improvement in the PGI2/TXA2 ratio in diabetic retinopathy by inhibition of thromboxane synthase
7-[(imidazol-1-yl)methyl]isoquinoline
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0.0054 mM, 50% inhibition
8-[2-(3-Pyridinyl)-1H-indol-1-yl]octanoic acid 1-(carboxymethyl)-3-[(1-carboxy-3-phenylpropyl)amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-5-yl ester
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9,11(Epoxymethano) prostanoic acid
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9,11-Azo-15-hydroxyprosta-5,13-dienoic acid
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-
9,11-Azoprosta-5,13 dienoic acid
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9,11-Azoprosta-5,13-dienoic acid
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9,11-Epoxymethano-15-hydroxy-prosta-5,13-dienoic acid
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9alpha,11alpha-Azo-15-(S)Hydroxyprosta-5(cis)-13(trans)-dienoic acid
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9alpha,11alpha-Methanoepoxy-15(S)-hydroxyprosta-5(cis)-13(trans)-dienoic acid
Benzydamine
-
-
BM 567
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i.e. 2-(cyclohexylamino)-5-nitro-N-[(pentylamino)carbonyl]-benzenesulfonamide, 10 microM, a specific inhibitor for thromboxane synthase, decrease the acitivity 2.1fold before diosgenin treatment
carboxyheptal imidazole
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10 microM, concentration of thromboxane B2 in culture supernatants: reduction of thromboxane B2 in prostate cancer cells PC-3 from 1295 pg/ml to 685 pg/ml, reduction of thromboxane B2 in erythroleukemia cells HEL from 580 pg/ml to 292 pg/ml. In PC-3 cell lysates reduction of thromboxane B2 level by 86%
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CGS 13080
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-
Chlorella powder
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the potent inhibition of cyclooxygenase-2 and thromboxane synthase contribute to the purported anti-inflmammatory and anti-thrombotic effect of Chlorella. This might be exploited for the prevention or treatment of several serious pathologies, including inflammatory diseases, immune and cancer
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clotrimazole
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as a heme ligand, molecular dynamics simulations of clotrimazole and 2-p-toluidinylnaphthalene-6-sulfonic acid-docking enzyme
Cu2+
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1 mM, complete inhibition
CV4151
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0.0000049 mM, 50% inhibition
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dazoxiben
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-
furegrelate
imidazole
indomethacin
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0.000017 mM, 50% inhibition of PGE2 formation, 0.000013 mM, 50% inhibition of 12-HHT formation
linoleic acid
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significant inhibition of cyclooxygenase/thromboxane synthase activity, determined by TXB2 production with an ELISA-based assay
linolelaidic acid
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significant inhibition of cyclooxygenase/thromboxane synthase activity, determined by TXB2 production with an ELISA-based assay
N-isopropyl-N'-[(2-(3'-methylphenylamino)-5-nitrobenzene)sulfonyl]urea
-
-
N-isopropyl-N'-[2-(3'-methylphenylamino)-5-nitrobenzenesulfonyl]urea
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0.001 mM, 95% inhibition
N-pentyl-N'-[(2-cyclohexylamino-5-nitrobenzene)sulfonyl]urea
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-
N-Substituted 3-(1H-imidazol-1-ylmethyl)indole carboxylic acid derivatives
-
-
-
N-tert-butyl-N'-(2-cyclohexylamino-5-nitrobenzenesulfonyl)urea
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-
N-tert-butyl-N'-[(2-(4'-methylphenylamino)-5-nitrobenzene)sulfonyl]urea
-
-
N-tert-butyl-N'-[(2-cyclohexylamino-5-nitrobenzene)sulfonyl]urea
-
-
NO
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irreversible in a concentration-dependent manner
OKY 1581
-
-
ozagrel
p-Benzyl-4-[1-oxo-2-(-chlorobenzyl)-3-phenylpropyl]phenyl phosphonate
paclitaxel
-
45% inhibition at 0.1 mM
prostaglandin H2
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suicide inactivation
R68070
-
0.0000015 mM, 50% inhibition
radical scavenging glycoprotein
-
-
ridogrel
-
0.000004 mM, 50% inhibition
samixogrel
-
0.000004 mM, 50% inhibition
Sodium 5-(3'-pyridinylmethyl)benzofuran-2-carboxylate
-
immobilized enzyme
Sodium 5-(3'pyridinylmethyl)benzofuran-2-carboxylate
-
-
Sodium p-benzyl-4-[1-oxo-2-(4-chlorobenzyl)-3-phenyl propyl]phenyl phosphonate
-
-
-
thromboxane A2
-
the production of thromboxane A2 by the enzyme is self-limiting, the enzyme is inactivated during the reaction
UK 36248
-
-
-
UK 37,248
-
-
Zn2+
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1 mM, 50% inhibition
[3-[[Hydroxy[4-[3-methyl-2-(3-pyridinyl)indol-1-yl]butyl]phosphinyl]oxy]2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-yl]acetic acid
-
-
[4-[3-Methyl-2-(3-pyridinyl)-1H-indol-1-yl]butyl]phosphonic acid
-
-
[4-[3-Methyl-2-(3-pyridinyl)-1H-indol-1-yl]butyl]phosphonic acid monoethyl ester
-
-
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
diosgenin
-
10 microM increases cyclooxygenase-2 and thromboxane synthase expression and activities in HEL cells, 3.5fold at 96 h and 4.5fold at 144 h
phosphatidylcholine
-
-
phosphatidylethanolamine
-
-
phosphatidylserine
-
-
additional information
-
the catalytic activities of the binary phosphatidylethanolamine/phosphatidylcholine and phosphatidylserine/phosphatidylcholine and ternary phosphatidylcholine/phosphatidylethanolamine/phosphatidylserine are similar and increase relative to the unary phosphatidylcholine system
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.02 - 0.022
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
0.071 - 0.087
15-hydroperoxyeicosatetraenoic acid
0.012
15-hydroxy-9alpha,11alpha-peroxiprosta-5,13-dienoic acid
-
-
-
0.023
prostaglandin G2
-
prostaglandin H3
0.024
Prostaglandin H1
-
-
0.002 - 0.022
prostaglandin H2
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.017
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
Homo sapiens
-
recombinant TXAS
28.2
prostaglandin G2
Homo sapiens
-
-
26.7 - 27.1
prostaglandin H2
20.4 - 59.4
Prostaglandin H3
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1
12L-Hydroperoxy-5,8,10,14-eicosatetraenoic acid
-
-
1
Zn2+
-
-
additional information
Chlorella powder
-
3.32 microg/ml, tested in an in vitro assay system
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00515
-
-
0.231
-
-
0.255
-
-
0.259
-
-
1.15
-
-
2.95
-
recombinant TXAS
24.1
-
-
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
-
broad
7.5
-
-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 8.5
-
very little pH-dependence between pH 5-8.5, above pH 9.0 the reaction is significantly depressed
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
-
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20 - 37
-
activity at 37°C is not significantly higher than at 20°C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
low activity
Manually annotated by BRENDA team
-
bladder cancer cell lines T24 and TCC-SUP
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
colorectal carcinoma
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
human erythroleukemia cells
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
mouse leydig cells
Manually annotated by BRENDA team
-
a squamous cell carcinoma cell line
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
58000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
x * 58000, SDS-PAGE
additional information
-
enzyme structure molecular homology modeling using the crystal structure of human microsomal CYP3A4, PDB entry 1TQN, as the template structure
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5
-
unstable below
3200
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
52
-
5 min, 50% loss of activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
immobilized enzyme is inactivated at pH 3.0
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70°C, stable for several months
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
immunoaffinity purification
-
intrinsic membrane protein, detergent treatment is necessary
-
one-step immunoaffinity purification
-
partial
recombinant C-terminally His-tagged modified enzyme from Escherichia coli strain DH5alpha by nickel affinity chromatography
-
recombinant His-tagged TXAS
-
recombinant TXAS
-
recombinant TXAS, Ni-NTA, column, DEAE-column, Octyl-column
-
recombinant wild-type and mutant C-terminally His4-tagged modified enzyme from Escherichia coli strain BL21/(DE3)pLys by nickel affinity and hydroxyapatite chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
characterization of the gene TBXAX1 encoding thromboxane synthase
-
expression in Escherichia coli
-
expression of C-terminally His-tagged enzyme replacing the first 29 amino acid residues in the N-terminal transmembrane domain with the hydrophilic sequence MAKKTSS for TXAS cDNA in Escherichia coli strain DH5alpha
-
expression of wild-type and mutant C-terminally His4-tagged enzyme replacing the first 28 amino acid residues in the N-terminal transmembrane domain with the hydrophilic sequence MAKKTSS for TXAS cDNA in Escherichia coli strain BL21/(DE3)pLys
-
overexpression in Escherichia coli
-
stable overexpression of thromboxane synthase in SKMES-1 cells
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
4 weeks of streptozotocin-induced diabetes do not increase the retinal levels of TxS
after 8 and 16 weeks on the fat diet, aortic arches from low-density lipoprotein receptor deficient mice show a significant increase in TXAS mRNA level when compared with control
-
an overall increase in TXS expression is observed in tumor tissues relative to normal, increased TXS expression at mRNA level is reported in renal cell carcinoma, breast carcinoma, prostate cancer and uterine cancer when compared with matched normal tissues
-
inhibition of platelet TXA2 generation (acetylsalicylic acid), lowering of cholesterol (statins), inhibition of platelet aggregation (clopidogrel), or promoting vasodilatation (dipyridamole) has no effect on TXAS mRNA expression levels
smokers tend to express more TxAS than nonsmokers
-
TNF-alpha, U46619 and 8-isoprostane F2alpha and hypoxia all augment TXAS protein expression. NADPH oxidase-1 (but not NADPH oxidase-4) gene silencing, as well as picotamide and iloprost inhibit the increase in TXAS expression and activity
-
TXAS increases in atherosclerotic lesions of patients with recent symptoms of thrombotic events
-
TXAS mRNA expression is increased within the vascular wall in mouse models of atherosclerosis with advanced lesions
-
TXSA is upregulated in human glial tumors
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A408L
-
42% of wild-type activity
A415V
-
82% of wild-type activity
C480H
-
no activity
C480S
-
no activity
C480Y
-
no activity
E134D
-
35% of wild-type activity
E135D
-
123% of wild-type activity
E414D
-
39% of wild-type activity
F409Y
-
42% of wild-type activity
F411Y
-
38% of wild-type activity
L488P
-
in alpha-helix, indroducing a coil in the secondary structure, crucial for enzyme activity
L83P
-
in beta-sheet, indroducing a coil in the secondary structure, crucial for enzyme activity
N110I
-
no activity
Q482W
-
changing an aliphatic amino acid with low steric hindrance into an aromatic amino acid with high steric hindrance in the vicinitx of the catalytic site, modifying the interaction of the enzyme-substarte complex, crucial for enzyme activity
R137A
-
2% of wild-type activity
R137K
-
5% of wild-type activity
R410G
-
46% of wild-type activity
R413K
-
1% of wild-type activity
R431E
-
decreased enzyme activity, 1% residual activity
R431K
-
decreased enzyme activity, 1% residual activity
R478A
-
no activity
T412S
-
41% of wild-type activity
V136A
-
69% of wild-type activity
W203F
-
site-directed mutagenesis, ligand binding analysis compared to the wild-type enzyme
W31F
-
site-directed mutagenesis, ligand binding analysis compared to the wild-type enzyme
W31F/W65F/W133F/W203F/W466F
-
site-directed mutagenesis, ligand binding analysis compared to the wild-type enzyme
W466F
-
site-directed mutagenesis, ligand binding analysis compared to the wild-type enzyme
W65F
-
site-directed mutagenesis, ligand binding analysis compared to the wild-type enzyme
additional information
-
treatment with enzyme-specific RNAi results in increased levels of steroidogenic acute regulatory protein StAR and steroidogenesis. Inhibition of enzyme activity reduces the levels of StaR transcriptional repressor DAX-1
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
medicine
pharmacology