1.14.99.1: prostaglandin-endoperoxide synthase
This is an abbreviated version!
For detailed information about prostaglandin-endoperoxide synthase, go to the full flat file.
Word Map on EC 1.14.99.1
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1.14.99.1
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arachidonic
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indomethacin
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necrosis
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nsaid
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tnf
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lipopolysaccharide
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endothelial
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nonsteroidal
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celecoxib
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artery
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thromboxane
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aspirin
-
lps
-
lipoxygenase
-
pain
-
cardiovascular
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lps-induced
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platelet
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prostanoids
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agonist
-
gastrointestinal
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mapks
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phospholipase
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gastric
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carcinogenesis
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eicosanoids
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leukotriene
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ulcer
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arthritis
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analgesic
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prostacyclin
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nf-kappab
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lps-stimulated
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colorectal
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angiogenesis
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edema
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tnf-alpha
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ibuprofen
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vasodilator
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il-1beta
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osteoarthritis
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nonselective
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factor-alpha
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chemopreventive
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lipopolysaccharide-induced
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factor-kappa
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endothelium-dependent
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vasoconstriction
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l-name
-
endothelium-derived
-
medicine
- 1.14.99.1
-
arachidonic
- indomethacin
- necrosis
-
nsaid
- tnf
- lipopolysaccharide
- endothelial
-
nonsteroidal
- celecoxib
- artery
-
thromboxane
- aspirin
- lps
- lipoxygenase
- pain
- cardiovascular
-
lps-induced
- platelet
-
prostanoids
- agonist
- gastrointestinal
- mapks
- phospholipase
- gastric
- carcinogenesis
-
eicosanoids
-
leukotriene
- ulcer
- arthritis
-
analgesic
- prostacyclin
- nf-kappab
-
lps-stimulated
- colorectal
- angiogenesis
- edema
- tnf-alpha
- ibuprofen
-
vasodilator
- il-1beta
- osteoarthritis
-
nonselective
- factor-alpha
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chemopreventive
-
lipopolysaccharide-induced
-
factor-kappa
-
endothelium-dependent
-
vasoconstriction
-
l-name
-
endothelium-derived
- medicine
Reaction
Synonyms
(PG)H synthase, COX, COX-1, COX-2, COX1, Cox2, cyclooxygenase, cyclooxygenase 1, cyclooxygenase 2, cyclooxygenase-1, cyclooxygenase-1b, cyclooxygenase-2, cycloxigenase-2, fatty acid cyclooxygenase, hPGHS-1, hPGHS-2, oPGHS-1, PG G/H synthase 2, PG H synthase, PG synthetase, PG-endoperoxide synthase 2, PG-endoperoxide synthetase, PGH-synthase, PGHS, PGHS isoform-1, PGHS-1, PGHS-2, PHS, PHS-1, PHS-2, prostagladin-H synthase, prostaglandin endoperoxide H synthase, prostaglandin endoperoxide H synthase 1, prostaglandin endoperoxide H synthase 2, prostaglandin endoperoxide H synthase-1, prostaglandin endoperoxide H2 synthase-2, prostaglandin endoperoxide synthase, prostaglandin endoperoxide synthase 2, prostaglandin endoperoxide synthase-1, prostaglandin endoperoxide synthase-2, prostaglandin endoperoxide synthetase, prostaglandin G/H synthase, prostaglandin G/H synthase-2, prostaglandin H synthase, prostaglandin H synthase-1, prostaglandin H synthase-2, prostaglandin H2 synthase, prostaglandin H2 synthase-1, prostaglandin synthase, prostaglandin synthase-2, prostaglandin synthetase, prostaglandin-endoperoxide synthase, prostaglandin-endoperoxide synthase 1, prostaglandin-endoperoxide synthase 2, prostaglandin-H-synthase, prostaglandin-H-synthase 1, prostaglandin-H-synthase 2, PTGS 2, PTGS-1, PTGS-2, PTGS1, PTGS2, putative cyclooxygenase-3, synthase, prostaglandin, tPGHS-1, tPGHS-2
ECTree
1.14.99.1 prostaglandin-endoperoxide synthaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.14.99.1 - prostaglandin-endoperoxide synthase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid + AH2 + O2
? + A + H2O
substrate binding structure and nonproductive conformation, overview
-
-
?
arachidonate + reduced N,N,N',N'-tetramethylphenylenediamine + 2 O2
prostaglandin G2 + oxidized N,N,N',N'-tetramethylphenylenediamine + ?
-
-
-
?
arachidonate + reduced N,N,N',N'-tetramethylphenylenediamine + 2 O2
prostaglandin H2 + oxidized N,N,N',N'-tetramethylphenylenediamine + H2O
arachidonic acid + 2 O2
prostaglandin G2
cyclooxygenase reaction, arachidonic acid as electron donor
-
-
?
arachidonic acid + 3,4-methylenedioxyamphetamine
?
-
postulated bioactivation to a neurodegenerative free radical intermediate that can initiate the formation of reactive oxygen species
-
-
?
arachidonic acid + 3,4-methylenedioxymethamphetamine
?
-
postulated bioactivation to a neurodegenerative free radical intermediate that can initiate the formation of reactive oxygen species
-
-
?
arachidonic acid + AH2 + 2 O2
15-hydroperoxy-9alpha,11alpha-peroxidoprosta-5,13-dienoic acid + A + H2O
-
-
-
?
arachidonic acid + AH2 + 2 O2
6-keto-prostaglandin F1alpha + A + H2O
-
activity assay
-
-
?
arachidonic acid + methamphetamine
?
-
postulated bioactivation to a neurodegenerative free radical intermediate that can initiate the formation of reactive oxygen species
-
-
?
arachidonic acid + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
-
r
H2O2 + N,N,N',N'-tetramethyl-p-phenylenediamine
?
-
peroxidase activity
-
-
?
linoleic acid + AH2 + O2
9-hydroxyoctadecadienoic acid + 13-hydroxyoctadecadienoic acid + ?
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid + AH2 + O2
? + A + H2O
the substrate is bound in the cyclooxygenase channel of COX-2, binding structure, overview. The carboxylate of docosahexaenoate interacts with Arg120 and Tyr355 at the base of the channel and the omega-end abuts the side chain of Ile377 near Gly533 in the hydrophobic groove above Ser530
-
-
?
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid + AH2 + O2
? + A + H2O
-
-
-
?
8,11,14-eicosatrienoic acid + O2
prostaglandin G1 + ?
-
bis-dioxygenase activity, cyclooxygenase activity, presence of hematin
9alpha,11alpha-epidioxy-15(S)-hydroperoxy-13-trans-prostenoic acid
?
8,11,14-eicosatrienoic acid + O2
prostaglandin H1 + ?
-
hydroperoxidase activity, presence of hematin and tryptophan
-
-
?
arachidonate + AH2 + 2 O2
prostaglandin G2 + A + ?
-
-
-
?
arachidonate + AH2 + 2 O2
prostaglandin H2 + A + H2O
-
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
-
-
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
the reaction comprises two steps: dioxygenation of arachidonate to yield prostaglandin G2 containing both a 9-11 endoperoxide and a 15-peroxide group, and a peroxidase reaction, which converts prostaglandin G2 to prostaglandin H2 where the 15-peroxide is reduced to an alcohol
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
substrate binding structure and nonproductive conformation, overview
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
-
-
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
the reaction comprises two steps: dioxygenation of arachidonate to yield prostaglandin G2 containing both a 9-11 endoperoxide and a 15-peroxide group, and a peroxidase reaction, which converts prostaglandin G2 to prostaglandin H2 where the 15-peroxide is reduced to an alcohol
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
-
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
-
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
-
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
cyclooxygenase activity
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
-
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
-
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
-
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
-
-
-
?
arachidonate + reduced N,N,N',N'-tetramethylphenylenediamine + 2 O2
prostaglandin H2 + oxidized N,N,N',N'-tetramethylphenylenediamine + H2O
-
-
-
?
arachidonate + reduced N,N,N',N'-tetramethylphenylenediamine + 2 O2
prostaglandin H2 + oxidized N,N,N',N'-tetramethylphenylenediamine + H2O
-
-
-
?
arachidonate + reduced N,N,N',N'-tetramethylphenylenediamine + 2 O2
prostaglandin H2 + oxidized N,N,N',N'-tetramethylphenylenediamine + H2O
-
-
-
?
arachidonic acid + AH2 + 2 O2
15(R)-hydroxy-eicosatetraenoic acid + A + H2O
-
-
product of aspirin acetylated enzyme or S516M mutant
?
arachidonic acid + AH2 + 2 O2
15(R)-hydroxy-eicosatetraenoic acid + A + H2O
-
-
product of aspirin treated enzyme
?
cis-5,8,11,14,17-eicosapentaenoic acid + reduced acceptor + O2
?
-
-
-
r
cis-7,10,13,16-docosatetraenoic acid + reduced acceptor + O2
?
-
-
-
r
cis-8,11,14-eicosatrienoic acid + reduced acceptor + O2
?
-
-
-
r
linoleic acid + AH2 + O2
9-hydroxyoctadecadienoic acid + 13-hydroxyoctadecadienoic acid + ?
-
-
-
?
linoleic acid + AH2 + O2
9-hydroxyoctadecadienoic acid + 13-hydroxyoctadecadienoic acid + ?
-
-
-
?
additional information
?
-
-
major products of arachidonic acids are prostaglandins D2 and E2, minor products prostaglandin F2alpha and 6-keto-prostaglandin F1alpha
-
-
?
additional information
?
-
-
dopamine precursor L-dihydroxyphenylalanine, i.e. L-DOPA, and metabolites dihydroxyphenylacetic acid, homovanillic acid, and 3-methoxytyramine may serve as substrates for prostaglandin H synthase-catalyzed bioactivation to free radical intermediates
-
-
?
additional information
?
-
activity with arachidonate in presence of glutathione leads to formation of malondialdehyde and (15S)-8-iso-prostaglandin F2alpha
-
-
?
additional information
?
-
activity with arachidonate in presence of glutathione leads to formation of malondialdehyde and (15S)-8-iso-prostaglandin F2alpha
-
-
?
additional information
?
-
PGHS-1 also exhibits peroxidase activity
-
-
?
additional information
?
-
PGHS-1 also exhibits peroxidase activity
-
-
?
additional information
?
-
PGHS-2 also exhibits peroxidase activity
-
-
?
additional information
?
-
PGHS-2 also exhibits peroxidase activity
-
-
?
additional information
?
-
-
relative activities of isozymes 1,2 depend on source of arachidonic acid - exogenous versus endogenous
-
-
?
additional information
?
-
although arachidonic acid is the preferred substrate, other fatty acids are oxygenated by the isozymes with varying efficiencies. The substrates bind in different conformations in each monomer constituting the homodimer in their respective structures such that one monomer exhibits nonproductive binding and the other productive binding of the substrate in the cyclooxygenase channel, Arg120 and Leu531 play a role, overview
-
-
?
additional information
?
-
-
although arachidonic acid is the preferred substrate, other fatty acids are oxygenated by the isozymes with varying efficiencies. The substrates bind in different conformations in each monomer constituting the homodimer in their respective structures such that one monomer exhibits nonproductive binding and the other productive binding of the substrate in the cyclooxygenase channel, Arg120 and Leu531 play a role, overview
-
-
?
additional information
?
-
-
electron donors used by hydroperoxidase: phenylbutazone, sulindac
-
-
?
additional information
?
-
-
formation of prostaglandin E2, prostaglandin F2alpha and prostaglandin D2 from arachidonic acid
-
-
?
additional information
?
-
-
electron donors used by hydroperoxidase: phenylbutazone, sulindac
-
-
?
additional information
?
-
-
electron donors used by hydroperoxidase: phenylbutazone, sulindac
-
-
?
additional information
?
-
-
xenobiotics such as benzo(a)pyrene cannot act as electron donor, but undergo cooxydation during hydroperoxidase reaction
-
-
?
additional information
?
-
-
functional differentiation of cyclooxygenase and peroxidase activities by trypsin treatment
-
-
?
additional information
?
-
-
cooxidation of: 4-chloroaniline to yield N-(4-chlorophenyl)-hydroxylamine and 1-chloro-4-nitrosobenzene
-
-
?
additional information
?
-
-
also catalyzed: transformation of arachidonic acid into prostaglandin E2, prostaglandin F2 alpha and 12-hydroxy-5,8,10-heptadecatrienoic acid
-
-
?
additional information
?
-
-
enzyme has a central position in prostanoic metabolism: first step in formation of prostaglandins and thromboxanes, the conversion of arachidonic acid to prostaglandin endoperoxides G and H
-
-
?
additional information
?
-
prostaglandin synthesis within the fetal central nervous system is critical for the the modulation of hypotension-induced fetal ACTH secretion involving PGHS-2, overview
-
-
?
additional information
?
-
prostaglandin synthesis within the fetal central nervous system is critical for the the modulation of hypotension-induced fetal ACTH secretion involving PGHS-2, overview
-
-
?
additional information
?
-
-
prostaglandin synthesis within the fetal central nervous system is critical for the the modulation of hypotension-induced fetal ACTH secretion involving PGHS-2, overview
-
-
?
additional information
?
-
-
maximal values of the initial reaction rate and yield of the product are attained at oxygen concentration 0.05 mM
-
-
?
additional information
?
-
-
the expression of PGHS-2 may be involved in inhibiting progesterone production
-
-
?
