1.1.1.188: prostaglandin-F synthase

This is an abbreviated version, for detailed information about prostaglandin-F synthase, go to the full flat file.

Reaction

(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate
+
NADP+
=
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
+
NADPH
+
H+

Synonyms

20alpha-HSD/PGFS, 20alpha-hydroxysteroid dehydrogenase/prostaglandin F-synthase, AKR1B1, AKR1B3, AKR1B7, AKR1C3, aldo-keto reductase, aldo-keto reductase 1C3, ALDR1, ALR2, DD1, dihydrodiol dehydrogenase 1, m-PGFS, More, NADPH-dependent prostaglandin D2 11-keto reductase, PG endoperoxide reductase, PGD 11-ketoreductase, PGD2 11-ketoreductase, PGD2 11-ketoreductase activity, PGF synthase, PGF synthase I, PGF synthase II, PGF2alpha synthase, PGF2alpha-synthetic activity, PGFS, PGFS I, PGFS-I, PGFS-II, PGFSI, PGFSII, PGH 9-,11-endoperoxide reductase, PGH2 9,11-endoperoxidase, PGH2 9,11-endoperoxide reductase, PGH2 9-,11-endoperoxide reductase, prostaglandin 11-keto reductase, prostaglandin 11-ketoreductase, prostaglandin D2 11-ketoreductase, prostaglandin D2-ketoreductase, prostaglandin F synthase, prostaglandin F synthase I, prostaglandin F synthase II, prostaglandin F synthetase, prostaglandin F2alpha synthase, prostaglandin F2alpha-synthase, prostaglandin-D2 11-reductase, prostaglandin-F2alpha synthase, prostamide/PGF synthase, prostamide/prostaglandin F synthase, reductase, 15-hydroxy-11-oxoprostaglandin, synthetase, prostaglandin F2alpha, type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase, vas deferens protein

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.188 prostaglandin-F synthase

Reference

Reference on EC 1.1.1.188 - prostaglandin-F synthase

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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Endo, K.; Fukui, M.; Mishima, M.; Watanabe, K.
Metabolism of vitamin A affected by prostaglandin F synthase in contractile interstitial cells of bovine lung
Biochem. Biophys. Res. Commun.
287
956-961
2001
Bos taurus
Manually annotated by BRENDA team
Suzuki-Yamamoto, T.; Toida, K.; Tsuruo, Y.; Watanabe, K.; Ishimura, K.
Immunocytochemical localization of lung-type prostaglandin F synthase in the rat spinal cord
Brain Res.
877
391-395
2000
Rattus norvegicus
Manually annotated by BRENDA team
Kubata, B.K.; Duszenko, M.; Kabututu, Z.; Rawer, M.; Szallies, A.; Fujimori, K.; Inui, T.; Nozaki, T.; Yamashita, K.; Horii, T.; Urade, Y.; Hayaishi, O.
Identification of a novel prostaglandin F2.alpha. synthase in Trypanosoma brucei
J. Exp. Med.
192
1327-1337
2000
Trypanosoma brucei
Manually annotated by BRENDA team
Asselin, E.; Fortier, M.A.
Detection and regulation of the messenger for a putative bovine endometrial 9-keto-prostaglandin E2 reductase: effect of oxytocin and interferon-tau
Biol. Reprod.
62
125-131
2000
Bos taurus
Manually annotated by BRENDA team
Suzuki-Yamamoto, T.; Nishizawa, M.; Fukui, M.; Okuda-Ashitaka, E.; Nakajima, T.; Ito, S.; Watanabe, K.
cDNA cloning, expression and characterization of human prostaglandin F synthase
FEBS Lett.
462
335-340
1999
Homo sapiens
Manually annotated by BRENDA team
Suzuki, T.; Fujii, Y.; Miyano, M.; Chen, L.Y.; Takahashi, T.; Watanabe, K.
cDNA cloning, expression, and mutagenesis study of liver-type prostaglandin F synthase
J. Biol. Chem.
274
241-248
1999
Bos taurus
Manually annotated by BRENDA team
Xiao, C.W.; Murphy, B.D.; Sirois, J.; Goff, A.K.
Down-regulation of oxytocin-induced cyclooxygenase-2 and prostaglandin F synthase expression by interferon-.tau. in bovine endometrial cells
Biol. Reprod.
60
656-663
1999
Bos taurus
Manually annotated by BRENDA team
Fukui, M.; Fujimoto, T.; Watanabe, K.; Endo, K.; Kuno, K.
Prostaglandin F synthase is localized to contractile interstitial cells in bovine lung
J. Histochem. Cytochem.
44
251-257
1996
Bos taurus
Manually annotated by BRENDA team
Barski, O.A.; Watanabe, K.
Kinetic mechanism of ketoreductase activity of prostaglandin F synthase from bovine lung
FEBS Lett.
320
107-110
1993
Bos taurus
Manually annotated by BRENDA team
Kuchinke, W.; Barski, O.; Watanabe, K.; Hayaishi, O.
A lung type prostaglandin F synthase is expressed in bovine liver: cDNA sequence and expression in E. coli
Biochem. Biophys. Res. Commun.
183
1238-1246
1992
Bos taurus
Manually annotated by BRENDA team
Chen, L.Y.; Watanabe, K.; Hayaishi, O.
Purification and characterization of prostaglandin F synthase from bovine liver
Arch. Biochem. Biophys.
296
17-26
1992
Bos taurus
Manually annotated by BRENDA team
Watanabe, K.; Fujii, Y.; Ohkubo, H.; Kuramitsu, S.; Kagamiyama, H.; Nakanishi, S.; Hayaishi, O.
Expression of bovine lung prostaglandin F synthase in Escherichia coli
Biochem. Biophys. Res. Commun.
181
272-278
1991
Bos taurus
Manually annotated by BRENDA team
Watanabe, K.; Fujii, Y.; Nakayama, K.; Ohkubo, H.; Kuramitsu, S.; Hayashi, H.; Kagamiyama, H.; Nakanishi, S.; Hayaishi, O.
Cloning, nucleotide sequence and gene expression of bovine lung prostaglandin F synthetase
Adv. Prostaglandin Thromboxane Leukot. Res.
19
462-465
1988
Bos taurus
Manually annotated by BRENDA team
Wolfe, L.S.; Rostworowski, K.; Pellerin, L.; Sherwin, A.
Metabolism of prostaglandin D2 by human cerebral cortex into 9alpha,11beta-prostaglandin F2 by an active NADPH-dependent 11-ketoreductase:Metabolism of prostaglandin D2 by human cerebral cortex into 9alpha,11beta-prostaglandin F2 by an active NADPH-dependent 11-ketoreductase
J. Neurochem.
53
64-70
1989
Homo sapiens
Manually annotated by BRENDA team
Watanabe, K.; Fujii, Y.; Nakayama, K.; Ohkubo, H.; Karamitsu, S.; Kagamiyama, H.; Nakanishi, S.; Hayaishi, O.
Structural similarity of bovine lung prostaglandin F synthase to lens epsilon-crystallin of the European common frog
Proc. Natl. Acad. Sci. USA
85
11-15
1988
Bos taurus, Rana temporaria
Manually annotated by BRENDA team
Goh, Y.; Urade, Y.; Fujimoto, N.; Hayaishi, O.
Content and formation of prostaglandins and distribution of prostaglandin-related enzyme activities in the rat ocular system
Biochim. Biophys. Acta
921
302-311
1987
Rattus norvegicus
Manually annotated by BRENDA team
Watanabe, K.; Yoshida, R.; Shimizu, T.; Hayaishi, O.
Enzymatic formation of prostaglandin F2 alpha from prostaglandin H2 and D2. Purification and properties of prostaglandin F synthetase from bovine lung
J. Biol. Chem.
260
7035-7041
1985
Bos taurus
Manually annotated by BRENDA team
Wong, P.Y.K.
Purification of PGD2 11-ketoreductase from rabbit liver
Methods Enzymol.
86
117-125
1982
Oryctolagus cuniculus
Manually annotated by BRENDA team
Wong, P.Y.K.
Purification and partial characterization of prostaglandin D2 11-keto reductase in rabbit liver
Biochim. Biophys. Acta
659
169-178
1981
Oryctolagus cuniculus
Manually annotated by BRENDA team
Reingold, D.F.; Kawasaki, A.; Needleman, P.
A novel prostaglandin 11-keto reductase found in rabbit liver
Biochim. Biophys. Acta
659
179-188
1981
Oryctolagus cuniculus
Manually annotated by BRENDA team
Watanabe, K.; Shimizu, T.; Hayaishi, O.
Enzymic conversion of prostaglandin D2 to F2alpha in the rat lung
Biochem. Int.
2
603-610
1981
Rattus norvegicus
-
Manually annotated by BRENDA team
Suzuki-Yamamoto, T.; Fujii, Y.; Miyano, M.; Chen, L.Y.; Takahashi, T.; Yokoi, H.; Tsuruo, Y.; Ishimura, K.; Watanabe, K.
cDNA cloning and mutagenesis study of liver-type prostaglandin F synthase, and identification of the prostaglandin F producing cells in the liver
Adv. Exp. Med. Biol.
507
263-268
2002
Bos taurus
Manually annotated by BRENDA team
Koda, N.; Tsutsui, Y.; Niwa, H.; Ito, S.; Woodward, D.F.; Watanabe, K.
Synthesis of prostaglandin F ethanolamide by prostaglandin F synthase and identification of Bimatoprost as a potent inhibitor of the enzyme: new enzyme assay method using LC/ESI/MS
Arch. Biochem. Biophys.
424
128-136
2004
Homo sapiens, Homo sapiens (P42330)
Manually annotated by BRENDA team
Komoto, J.; Yamada, T.; Watanabe, K.; Takusagawa, F.
Crystal structure of human prostaglandin F synthase (AKR1C3)
Biochemistry
43
2188-2198
2004
Homo sapiens, Homo sapiens (P42330)
Manually annotated by BRENDA team
Nakashima, K.; Ueno, N.; Kamei, D.; Tanioka, T.; Nakatani, Y.; Murakami, M.; Kudo, I.
Coupling between cyclooxygenases and prostaglandin F(2alpha) synthase. Detection of an inducible, glutathione-activated, membrane-bound prostaglandin F2alpha-synthetic activity
Biochim. Biophys. Acta
1633
96-105
2003
Homo sapiens, Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team
Suzuki-Yamamoto, T.; Toida, K.; Watanabe, K.; Ishimura, K.
Immunocytochemical localization of prostaglandin F synthase II in the rat spinal cord
Brain Res.
969
27-35
2003
Rattus norvegicus
Manually annotated by BRENDA team
Lovering, A.L.; Ride, J.P.; Bunce, C.M.; Desmond, J.C.; Cummings, S.M.; White, S.A.
Crystal structures of prostaglandin D(2) 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin
Cancer Res.
64
1802-1810
2004
Homo sapiens (P42330)
Manually annotated by BRENDA team
Okano, Y.; Inoue, T.; Kubata, B.K.; Kabututu, Z.; Urade, Y.; Matsumura, H.; Kai, Y.
Crystallization and preliminary X-ray crystallographic studies of Trypanosoma brucei prostaglandin F2 alpha synthase
J. Biochem.
132
859-861
2002
Trypanosoma brucei
Manually annotated by BRENDA team
Watanabe, K.
Prostaglandin F synthase
Prostaglandins
68-69
401-407
2002
Bos taurus, Homo sapiens, Oryctolagus cuniculus, Ovis aries, Rattus norvegicus, Trypanosoma brucei
Manually annotated by BRENDA team
Franczak, A.; Woclawek-Potocka, I.; Oponowicz, A.; Kurowicka, B.; Kotwica, G.
Oxytocin stimulates prostaglandin F2alpha secretion and prostaglandin F synthase protein expression in porcine myometrial tissue
Reprod. Biol.
4
177-184
2004
Sus scrofa
Manually annotated by BRENDA team
Waclawik, A.; Rivero-Muller, A.; Blitek, A.; Kaczmarek, M.M.; Brokken, L.J.; Watanabe, K.; Rahman, N.A.; Ziecik, A.J.
Molecular cloning and spatiotemporal expression of prostaglandin F synthase and microsomal prostaglandin E synthase-1 in porcine endometrium
Endocrinology
147
210-221
2006
Sus scrofa (Q2TJA5), Sus scrofa
Manually annotated by BRENDA team
Ueno, N.; Takegoshi, Y.; Kamei, D.; Kudo, I.; Murakami, M.
Coupling between cyclooxygenases and terminal prostanoid synthases
Biochem. Biophys. Res. Commun.
338
70-76
2005
Mus musculus
Manually annotated by BRENDA team
Sakurai, M.; Oishi, K.; Watanabe, K.
Localization of cyclooxygenases-1 and -2, and prostaglandin F synthase in human kidney and renal cell carcinoma
Biochem. Biophys. Res. Commun.
338
82-86
2005
Homo sapiens
Manually annotated by BRENDA team
Komoto, J.; Yamada, T.; Watanabe, K.; Woodward, D.F.; Takusagawa, F.
Prostaglandin F2alpha formation from prostaglandin H2 by prostaglandin F synthase (PGFS): crystal structure of PGFS containing bimatoprost
Biochemistry
45
1987-1996
2006
Homo sapiens, Homo sapiens (P42330)
Manually annotated by BRENDA team
Yang, W.; Ni, J.; Woodward, D.F.; Tang-Liu, D.D.; Ling, K.H.
Enzymatic formation of prostamide F2alpha from anandamide involves a newly identified intermediate metabolite, prostamide H2
J. Lipid Res.
46
2745-2751
2005
Homo sapiens
Manually annotated by BRENDA team
Schuler, G.; Teichmann, U.; Kowalewski, M.P.; Hoffmann, B.; Madore, E.; Fortier, M.A.; Klisch, K.
Expression of cyclooxygenase-II (COX-II) and 20alpha-hydroxysteroid dehydrogenase (20alpha-HSD)/prostaglandin F-synthase (PGFS) in bovine placentomes: implications for the initiation of parturition in cattle
Placenta
27
1022-1029
2006
Bos taurus
Manually annotated by BRENDA team
Kowalewski, M.P.; Mutembei, H.M.; Hoffmann, B.
Canine prostaglandin F2alpha receptor (FP) and prostaglandin F2alpha synthase (PGFS): Molecular cloning and expression in the corpus luteum
Anim. Reprod. Sci.
107
161-175
2008
Canis lupus familiaris, Canis lupus familiaris (Q5FYA7)
Manually annotated by BRENDA team
Byrns, M.C.; Steckelbroeck, S.; Penning, T.M.
An indomethacin analogue, N-(4-chlorobenzoyl)-melatonin, is a selective inhibitor of aldo-keto reductase 1C3 (type 2 3alpha-HSD, type 5 17beta-HSD, and prostaglandin F synthase), a potential target for the treatment of hormone dependent and hormone independent malignancies
Biochem. Pharmacol.
75
484-493
2008
Homo sapiens (P42330)
Manually annotated by BRENDA team
Suzuki-Yamamoto, T.; Sugimoto, Y.; Ichikawa, A.; Ishimura, K.
Co-localization of prostaglandin F synthase, cyclooxygenase-1 and prostaglandin F receptor in mouse Leydig cells
Histochem. Cell Biol.
128
317-322
2007
Mus musculus
Manually annotated by BRENDA team
Moriuchi, H.; Koda, N.; Okuda-Ashitaka, E.; Daiyasu, H.; Ogasawara, K.; Toh, H.; Ito, S.; Woodward, D.F.; Watanabe, K.
Molecular characterization of a novel type of prostamide/prostaglandin F synthase, belonging to the thioredoxin-like superfamily
J. Biol. Chem.
283
792-801
2008
Mus musculus, Sus scrofa (A9CQL8), Sus scrofa
Manually annotated by BRENDA team
Waclawik, A.; Ziecik, A.J.
Differential expression of prostaglandin (PG) synthesis enzymes in conceptus during peri-implantation period and endometrial expression of carbonyl reductase/PG 9-ketoreductase in the pig
J. Endocrinol.
194
499-510
2007
Sus scrofa
Manually annotated by BRENDA team
Wasielak, M.; Glowacz, M.; Kaminska, K.; Waclawik, A.; Bogacki, M.
The influence of embryo presence on prostaglandins synthesis and prostaglandin E2 and F2alpha content in corpora lutea during periimplantation period in the pig
Mol. Reprod. Dev.
75
1208-1216
2008
Sus scrofa
Manually annotated by BRENDA team
Dozier, B.L.; Watanabe, K.; Duffy, D.M.
Two pathways for prostaglandin F2 alpha synthesis by the primate periovulatory follicle
Reproduction
136
53-63
2008
Homo sapiens (P42330), Homo sapiens AKR1C3 (P42330), Macaca fascicularis, Macaca fascicularis AKR1C3
Manually annotated by BRENDA team
Byrns, M.; Penning, T.
Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): Role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs
Chem. Biol. Interact.
178
221-227
2009
Homo sapiens, Homo sapiens (P42330)
Manually annotated by BRENDA team
Inagaki, S.; Esaka, Y.; Deyashiki, Y.; Uno, B.; Hara, A.; Toyooka, T.
Human liver dihydrodiol dehydrogenase 1-catalyzed reaction generating 9alpha,11beta-prostaglandin F2 from prostaglandin D2 followed by micellar electrokinetic chromatography
J. Sep. Sci.
31
735-740
2008
Homo sapiens
Manually annotated by BRENDA team
Kabututu, Z.; Manin, M.; Pointud, J.C.; Maruyama, T.; Nagata, N.; Lambert, S.; Lefrancois-Martinez, A.M.; Martinez, A.; Urade, Y.
Prostaglandin F2alpha synthase activities of aldo-keto reductase 1B1, 1B3 and 1B7
J. Biochem.
145
161-168
2009
Homo sapiens, Homo sapiens (P15121), Homo sapiens (P42330), Mus musculus
Manually annotated by BRENDA team
Suzuki-Yamamoto, T.; Toida, K.; Sugimoto, Y.; Ishimura, K.
Colocalization of prostaglandin F2alpha receptor FP and prostaglandin F synthase-I in the spinal cord
J. Lipid Res.
50
1996-2003
2009
Rattus norvegicus
Manually annotated by BRENDA team
Wasielak, M.; Kaminska, K.; Bogacki, M.
Effect of the conceptus on uterine prostaglandin-F2alpha and prostaglandin-E2 release and synthesis during the periimplantation period in the pig
Reprod. Fertil. Dev.
21
709-717
2009
Sus scrofa
Manually annotated by BRENDA team
Yoshikawa, K.; Takei, S.; Hasegawa-Ishii, S.; Chiba, Y.; Furukawa, A.; Kawamura, N.; Hosokawa, M.; Woodward, D.F.; Watanabe, K.; Shimada, A.
Preferential localization of prostamide/prostaglandin F synthase in myelin sheaths of the central nervous system
Brain Res.
1367
22-32
2011
Mus musculus
Manually annotated by BRENDA team
Fujimori, K.; Ueno, T.; Nagata, N.; Kashiwagi, K.; Aritake, K.; Amano, F.; Urade, Y.
Suppression of adipocyte differentiation by aldo-keto reductase 1B3 acting as prostaglandin F2alpha synthase
J. Biol. Chem.
285
8880-8886
2010
Mus musculus
Manually annotated by BRENDA team
Phillips, R.J.; Al-Zamil, H.; Hunt, L.P.; Fortier, M.A.; Lopez Bernal, A.
Genes for prostaglandin synthesis, transport and inactivation are differentially expressed in human uterine tissues, and the prostaglandin F synthase AKR1B1 is induced in myometrial cells by inflammatory cytokines
Mol. Hum. Reprod.
17
1-13
2011
Homo sapiens
Manually annotated by BRENDA team
Gram, A.; Buechler, U.; Boos, A.; Hoffmann, B.; Kowalewski, M.P.
Biosynthesis and degradation of canine placental prostaglandins: prepartum changes in expression and function of prostaglandin F2alpha-synthase (PGFS, AKR1C3) and 15-prostaglandin dehydrogenase
Biol. Reprod.
89
002
2013
Canis lupus familiaris
Manually annotated by BRENDA team
Nagata, N.; Kusakari, Y.; Fukunishi, Y.; Inoue, T.; Urade, Y.
Catalytic mechanism of the primary human prostaglandin F2alpha synthase, aldo-keto reductase 1B1 - prostaglandin D2 synthase activity in the absence of NADP(H)
FEBS J.
278
1288-1298
2011
Homo sapiens, Homo sapiens (P15121), Mus musculus
Manually annotated by BRENDA team
Bresson, E.; Lacroix-Pepin, N.; Boucher-Kovalik, S.; Chapdelaine, P.; Fortier, M.A.
The prostaglandin F synthase activity of the human aldose reductase AKR1B1 brings new lenses to look at pathologic conditions
Front. Pharmacol.
3
98
2012
Homo sapiens, Homo sapiens (P15121)
Manually annotated by BRENDA team
Bresson, E.; Boucher-Kovalik, S.; Chapdelaine, P.; Madore, E.; Harvey, N.; Laberge, P.Y.; Leboeuf, M.; Fortier, M.A.
The human aldose reductase AKR1B1 qualifies as the primary prostaglandin F synthase in the endometrium
J. Clin. Endocrinol. Metab.
96
210-219
2011
Homo sapiens, Homo sapiens (P15121)
Manually annotated by BRENDA team
Liedtke, A.J.; Adeniji, A.O.; Chen, M.; Byrns, M.C.; Jin, Y.; Christianson, D.W.; Marnett, L.J.; Penning, T.M.
Development of potent and selective indomethacin analogues for the inhibition of AKR1C3 (Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase) in castrate-resistant prostate cancer
J. Med. Chem.
56
2429-2446
2013
Homo sapiens (P42330)
Manually annotated by BRENDA team
Siemieniuch, M.J.; Jursza, E.; Kowalewski, M.P.; Majewska, M.; Skarzynski, D.J.
Prostaglandin endoperoxide synthase 2 (PTGS2) and prostaglandins F2alpha and E2 synthases (PGFS and PGES) expression and prostaglandin F2alpha and E2 secretion following oestrogen and/or progesterone stimulation of the feline endometrium
Reprod. Domest. Anim.
48
72-78
2013
Felis catus (E2IGW3), Felis catus
Manually annotated by BRENDA team