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Information on EC 1.14.99.1 - prostaglandin-endoperoxide synthase and Organism(s) Mus musculus and UniProt Accession Q05769

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EC Tree
IUBMB Comments
This enzyme acts both as a dioxygenase and as a peroxidase.
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This record set is specific for:
Mus musculus
UNIPROT: Q05769
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Word Map
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The taxonomic range for the selected organisms is: Mus musculus
The enzyme appears in selected viruses and cellular organisms
Synonyms
cox-2, cyclooxygenase, cyclooxygenase-2, cox-1, cyclooxygenase 2, ptgs2, pghs-2, cyclooxygenase-1, prostaglandin synthetase, pghs-1, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
cyclooxygenase-2
-
prostaglandin endoperoxide synthase-2
-
(PG)H synthase
-
-
-
-
COX-1
-
-
COX-2
-
-
cyclooxygenase
-
-
-
-
cyclooxygenase 1
-
-
cyclooxygenase 2
-
-
fatty acid cyclooxygenase
-
-
-
-
PG synthetase
-
-
-
-
PHS-1
-
-
prostaglandin endoperoxide synthetase
-
-
-
-
prostaglandin G/H synthase
-
-
-
-
prostaglandin H synthase
-
-
prostaglandin synthase
-
-
-
-
prostaglandin synthase-2
-
-
-
-
prostaglandin synthetase
-
-
-
-
prostaglandin-endoperoxide synthase 1
-
-
prostaglandin-endoperoxide synthase 2
-
-
PTGS1
-
-
PTGS2
-
-
synthase, prostaglandin
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
-
oxidation
reduction
PATHWAY SOURCE
PATHWAYS
-
-, -, -, -
SYSTEMATIC NAME
IUBMB Comments
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate,hydrogen-donor:oxygen oxidoreductase
This enzyme acts both as a dioxygenase and as a peroxidase.
CAS REGISTRY NUMBER
COMMENTARY hide
39391-18-9
-
9055-65-6
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid + AH2 + O2
? + A + H2O
show the reaction diagram
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
-
-
?
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid + AH2 + O2
? + A + H2O
show the reaction diagram
substrate binding structure and nonproductive conformation, overview
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
show the reaction diagram
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
show the reaction diagram
-
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
show the reaction diagram
-
-
-
-
?
arachidonate + electron donor + O2
prostaglandin H2 + oxidized electron donor + H2O
show the reaction diagram
-
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
show the reaction diagram
-
-
-
-
?
arachidonic acid + 3,4-methylenedioxyamphetamine
?
show the reaction diagram
-
postulated bioactivation to a neurodegenerative free radical intermediate that can initiate the formation of reactive oxygen species
-
-
?
arachidonic acid + 3,4-methylenedioxymethamphetamine
?
show the reaction diagram
-
postulated bioactivation to a neurodegenerative free radical intermediate that can initiate the formation of reactive oxygen species
-
-
?
arachidonic acid + AH2 + 2 O2
15(R)-hydroxy-eicosatetraenoic acid + A + H2O
show the reaction diagram
-
-
product of aspirin treated enzyme
?
arachidonic acid + methamphetamine
?
show the reaction diagram
-
postulated bioactivation to a neurodegenerative free radical intermediate that can initiate the formation of reactive oxygen species
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
show the reaction diagram
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
show the reaction diagram
-
-
-
?
arachidonate + AH2 + O2
prostaglandin H2 + A + H2O
show the reaction diagram
-
-
-
-
?
arachidonate + reduced acceptor + O2
prostaglandin H2 + acceptor + H2O
show the reaction diagram
-
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3,6-bis(3-[[(furan-2-yl)methyl]amino]propyl)-9H-xanthen-9-one
-
3,6-bis(5-[[(furan-2-yl)methyl]amino]pentyl)-9H-xanthen-9-one
-
3,6-bis[3-(2-methyl-1H-indol-1-yl)propyl]-9H-xanthen-9-one
-
3,6-bis[3-(4-methylpiperazin-1-yl)propyl]-9H-xanthen-9-one
-
3,6-bis[3-(4-nitroanilino)propyl]-9H-xanthen-9-one
-
3,6-bis[3-(cyclohexylamino)propyl]-9H-xanthen-9-one
-
3,6-bis[3-(morpholin-4-yl)propyl]-9H-xanthen-9-one
-
3,6-bis[3-(piperidin-1-yl)propyl]-9H-xanthen-9-one
-
3,6-bis[3-[(1H-pyrazol-3-yl)amino]propyl]-9H-xanthen-9-one
-
3,6-bis[3-[(2-chloropyridin-3-yl)amino]propyl]-9H-xanthen-9-one
-
3,6-bis[3-[(4H-1,2,4-triazol-4-yl)amino]propyl]-9H-xanthen-9-one
-
3,6-bis[3-[(pyrazin-2-yl)amino]propyl]-9H-xanthen-9-one
-
3,6-bis[3-[(pyridin-2-yl)amino]propyl]-9H-xanthen-9-one
-
3,6-bis[4-(1H-imidazol-2-yl)butyl]-9H-xanthen-9-one
-
3,6-bis[5-(2-methyl-1H-indol-1-yl)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-(4-methylpiperazin-1-yl)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-(4-nitroanilino)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-(cyclohexylamino)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-(morpholin-4-yl)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-(piperidin-1-yl)pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(1H-pyrazol-3-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(2-chloropyridin-3-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(4H-1,2,4-triazol-4-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(piperidin-1-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(pyrazin-2-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[5-[(pyridin-2-yl)amino]pentyl]-9H-xanthen-9-one
-
3,6-bis[6-(1H-imidazol-2-yl)hexyl]-9H-xanthen-9-one
-
6-methoxy-2-naphthyl acetic acid
-
active metabolite of nabumetone, isozyme 1, 50% inhibition at 0.2-0.8 mM, isozyme 2, 50% inhibition at 0.015-0.55 mM
Acetylsalicylic acid
docosahexaenoic acid
-
isozyme 1, 50% inhibition at 0.011 mM, isozyme 2, 50% inhibition at 0.015 mM
flurbiprofen
-
isozyme 1, 50% inhibition at 0.0005 mM, isozyme 2, 50% inhibition at 0.003 mM
Ibuprofen
-
isozyme 1, 50% inhibition at 0.09 mM, isozyme 2, 50% inhibition at 0.008 mM
indomethacin
-
isozyme 1, 50% inhibition at 0.005 mM, isozyme 2, 50% inhibition at 0.130-0.160 mM
Meclofenamic acid
-
isozyme 1, 50% inhibition at 0.002 mM, isozyme 2, 50% inhibition at 0.015 mM
NS398
-
-
piroxicam
-
isozyme 1, 50% inhibition at 0.075 mM, isozyme 2, 50% inhibition at 0.002 mM
sulindac sulfide
-
isozyme 1, 50% inhibition at 0.0004 mM, isozyme 2, 50% inhibition at 0.012 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0368
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
0.00945
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
0.00295 - 0.00514
arachidonate
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3.45
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
8.7
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
27
arachidonate
pH 8.0, 25°C, COX-2 mutant N580A
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
9
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
920
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid
pH 8.0, 25°C, COX-2 mutant N580A
5240
arachidonate
pH 8.0, 25°C, COX-2 mutant N580A
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
cervical distensibility is decreased in enzyme knockout mice on the day of expected delivery. Delayed parturition in enzyme knockout mice is the result of impaired luteolysis and cervical dilation
physiological function
-
the enzyme promotes Col10a1 expression and enhances hypertrophic differentiation of ATDC5 cells. Cox-2 also upregulates marker genes of chondrocyte maturation, apoptosis, and matrix mineralization, including transcription factors Runx2, Alp, Bsp, and Osterix
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
PGH2_MOUSE
604
0
69013
Swiss-Prot
Secretory Pathway (Reliability: 2)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
65000
-
immunoblot
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
-
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
-
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
arachidonic acid, eicosapentaenoic acid, and docosahexaenoic acid bound to Co3+-protoporphyrin IX-reconstituted recombinant His-tagged isozyme COX-2 mutant N580A, 0.003 ml of 3 mg/ml protein in 25 mM Tris, pH 8.0, 150 mM NaCl, and 0.53% w/v beta-octylglucoside is mixed with 0.003 ml of reservoir solution containing 23-34% polyacrylic acid 5100, 100 mM HEPES, pH 7.5, 20 mM MgCl2, and 0.6% w/v beta-octylglucoside, equilibration over reservoir solution without beta-octylglucoside, 23°C, 3 days to 4 weeks, X-ray diffraction structure determination and analysis at 2.1 A, 2.4 A, and 2.65 A resolution, respectively
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
L531A
site-directed mutagenesis, the mutant shows reduced Vmax and Km with arachidonate compared to the wild-type COX-2
L531F
site-directed mutagenesis, the mutant shows reduced Vmax and Km with arachidonate compared to the wild-type COX-2
L531P
site-directed mutagenesis, the mutant shows reduced Vmax and Km with arachidonate compared to the wild-type COX-2
L531T
site-directed mutagenesis, the mutant shows reduced Vmax and Km with arachidonate compared to the wild-type COX-2
N580A
site-directed mutagenesis, crystal structure determination with bound substrates, overview
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged wild-type and mutant COX-2 proteins by nickel affinity chromatography and gel filtration
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression of His-tagged wild-type and mutant COX-2 proteins
RENATURED/Commentary
ORGANISM
UNIPROT
LITERATURE
the purified recombinant apoenzyme is reconstituted with Co3+-protoporphyrin IX and fatty acid substrate to generate the appropriate enzyme-substrate complexes for X-ray crystallographic analyses
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Ishii, R.; Horie, M.; Saito, K.; Arisawa, M.; Kitanaka, S.
Prostaglandin E(2) production and induction of prostaglandin endoperoxide synthase-2 is inhibited in a murine macrophage-like cell line, RAW 264.7, by Mallotus japonicus phloroglucinol derivatives
Biochim. Biophys. Acta
1571
115-123
2002
Mus musculus
Manually annotated by BRENDA team
Chulada, P.C.; Loftin, C.D.; Winn, V.D.; Young, D.A.; Tiano, H.F.; Eling, T.E.; Langenbach, R.
Relative activities of retrovirally expressed murine prostaglandin synthase-1 and -2 depend on source of arachidonic acid
Arch. Biochem. Biophys.
330
301-313
1996
Mus musculus
Manually annotated by BRENDA team
Meade, E.A.; Smith, W.L.; DeWitt, D.L.
Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti-inflammatory drugs
J. Biol. Chem.
268
6610-6614
1993
Mus musculus
Manually annotated by BRENDA team
Jeng, W.; Ramkissoon, A.; Parman, T.; Wells, P.G.
Prostaglandin H synthase-catalyzed bioactivation of amphetamines to free radical intermediates that cause CNS regional DNA oxidation and nerve terminal degeneration
FASEB J.
20
638-650
2006
Mus musculus
Manually annotated by BRENDA team
Vecchio, A.J.; Simmons, D.M.; Malkowski, M.G.
Structural basis of fatty acid substrate binding to cyclooxygenase-2
J. Biol. Chem.
285
22152-22163
2010
Mus musculus (Q05769), Mus musculus
Manually annotated by BRENDA team
Das, A.; Gogoi, U.; Kalita, J.; Sandilya, S.
Molecular docking study of a series of substituted xanthone derivatives as novel COX-2 inhibitors targeting prostaglandin endoperoxide synthase-2
Curr. Enzyme Inhib.
12
195-204
2016
Mus musculus (Q05769)
-
Manually annotated by BRENDA team
Herington, J.L.; OBrien, C.; Robuck, M.F.; Lei, W.; Brown, N.; Slaughter, J.C.; Paria, B.C.; Mahadevan-Jansen, A.; Reese, J.
Prostaglandin-endoperoxide synthase 1 mediates the timing of parturition in mice despite unhindered uterine contractility
Endocrinology
159
490-505
2017
Mus musculus
Manually annotated by BRENDA team
Li, N.; Wang, Q.; Zhu, T.; Qiao, L.; Zhang, F.; Mi, R.; Wang, B.; Chen, L.; Gu, J.; Lu, Y.; Zheng, Q.
In vitro functional characterization of prostaglandin-endoperoxide synthase 2 during chondrocyte hypertrophic differentiation
Oncotarget
7
36280-36292
2016
Mus musculus
Manually annotated by BRENDA team