1.1.1.149: 20alpha-hydroxysteroid dehydrogenase

This is an abbreviated version, for detailed information about 20alpha-hydroxysteroid dehydrogenase, go to the full flat file.

Reaction

17alpha,20alpha-dihydroxypregn-4-en-3-one
+
NAD(P)+
=
17alpha-hydroxyprogesterone
+
NAD(P)H
+
H+

Synonyms

20-alpha-HSD, 20-alpha-hydroxysteroid dehydrogenase, 20alpha-HSD, 20alpha-HSDH, 20alpha-hydroxy steroid dehydrogenase, 20alpha-hydroxysteroid dehydrogenase, 20alpha-hydroxysteroid oxidoreductase, 20alpha-OH-SDH, AKR1C1, AKR1C23, AKR1C3, aldo-keto reductase family 1 member C1, HSD1

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.149 20alpha-hydroxysteroid dehydrogenase

Reference

Reference on EC 1.1.1.149 - 20alpha-hydroxysteroid dehydrogenase

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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Strickler, R.C.; Tobias, B.; Covey, D.F.
Human placental 17beta-estradiol dehydrogenase and 20alpha-hydroxysteroid dehydrogenase. Two activities at a single enzyme active site
J. Biol. Chem.
256
316-321
1981
Homo sapiens
Manually annotated by BRENDA team
Noda, K.; Shiota, K.; Takahashi, M.
Purification and characterization of rat ovarian 20alpha-hydroxysteroid dehydrogenase
Biochim. Biophys. Acta
1079
112-118
1991
Rattus norvegicus, Rattus norvegicus Wistar-Imamichi
Manually annotated by BRENDA team
Krafft, A.E.; Hylemon, P.B.
Purification and characterization of a novel form of 20alpha-hydroxysteroid dehydrogenase from Clostridium scindens
J. Bacteriol.
171
2925-2932
1989
Clostridium scindens
Manually annotated by BRENDA team
Pongsawasdi, P.; Anderson, B.M.
Studies of the coenzyme binding site of rat ovarian 20alpha-hydroxysteroid dehydrogenase
Arch. Biochem. Biophys.
238
280-289
1985
Rattus norvegicus
Manually annotated by BRENDA team
Blomquist, C.H.; Lindemann, N.J.; Hakanson, E.Y.
17beta-Hydroxysteroid and 20alpha-hydroxysteroid dehydrogenase activities of human placental microsomes: kinetic evidence for two enzymes differing in substrate specificity
Arch. Biochem. Biophys.
239
206-215
1985
Homo sapiens
Manually annotated by BRENDA team
Pongsawasdi, P.; Anderson, B.M.
Inactivation of rat ovarian 20alpha-hydroxysteroid dehydrogenase by N-alkylmaleimides
Arch. Biochem. Biophys.
233
481-488
1984
Rattus norvegicus
Manually annotated by BRENDA team
Pongsawasdi, P.; Anderson, B.M.
Kinetic studies of rat ovarian 20alpha-hydroxysteroid dehydrogenase
Biochim. Biophys. Acta
799
51-58
1984
Rattus norvegicus
Manually annotated by BRENDA team
Robertson, W.R.; Frost, J.; Hoyer, P.E.; Weinkove, C.
20alpha-Hydroxysteroid dehydrogenase activity in the rat corpus luteum; a quantitative cytochemical study
J. Steroid Biochem.
17
237-243
1982
Rattus norvegicus
Manually annotated by BRENDA team
Mori, M.; Wiest, W.G.
Purification of rat ovary 20alpha-hydroxysteroid dehydrogenase by affinity chromatography
J. Steroid Biochem.
11
1443-1449
1979
Rattus norvegicus
Manually annotated by BRENDA team
Shikita, M.; Tsuneoka, K.
Non-oligomeric nature of porcine testicular 20alpha-hydroxysteroid dehydrogenase
FEBS Lett.
66
4-7
1976
Sus scrofa
Manually annotated by BRENDA team
Hatano-Sato, F.; Takagi, Y.; Shikita, M.
Hydrogen transfer from NADPH to steroid by testicular 20alpha-hydroxysteroid dehydrogenase: stereospecficity and isotope effect
J. Biochem.
74
1065-1067
1973
Sus scrofa
Manually annotated by BRENDA team
Sato, F.; Takagi, Y.; Shikita, M.
20alpha-Hydroxysteroid dehydrogenase of porcine testes
J. Biol. Chem.
247
815-823
1972
Sus scrofa
Manually annotated by BRENDA team
Pineda, J.A.; Murdock, G.L.; Watson, R.J.; Warren, J.C.
Stereospecificity of hydrogen transfer by bovine testicular 20alpha-hydroxysteroid dehydrogenase
J. Steroid Biochem.
33
1223-1228
1989
Bos taurus
Manually annotated by BRENDA team
Nakajin, S.; Kawai, Y.; Ohno, S.; Shinoda, M.
Purification and characterization of pig adrenal 20alpha-hydroxysteroid dehydrogenase
J. Steroid Biochem.
33
1181-1189
1989
Sus scrofa
Manually annotated by BRENDA team
Pineda, J.A.; Salinas, M.E.; Warren, J.C.
Purification and characterization of 20alpha-hydroxysteroid dehydrogenase from bull testis
J. Steroid Biochem.
23
1001-1006
1985
Bos taurus
Manually annotated by BRENDA team
Kersey, W.H.; Wilcox, R.B.
Stereochemistry of hydrogen transfer by rat ovary 20alpha-hydroxysteroid dehydrogenase
Biochemistry
9
1284-1286
1970
Rattus norvegicus
Manually annotated by BRENDA team
Kersey, W.H.
Molecular weight of 20alpha-hydroxysteroid dehydrogenase estimated by thin layer gel filtration chromatography on Sephadex G-200
Tex. J. Sci.
26
607-611
1975
Rattus norvegicus
-
Manually annotated by BRENDA team
Krafft, A.E.; Winter, J.; Bokkenheuser, V.D.; Hylemon, P.B.
Cofactor requirements of steroid-17-20-desmolase and 20alpha-hydroxysteroid dehydrogenase ativities in cell extracts of Clostridium scindens
J. Steroid Biochem.
28
49-54
1987
Clostridium scindens
Manually annotated by BRENDA team
Nancarrow, C.D.; Sharaf, M.A.; Sweet, F.
Purification of 20alpha-hydroxysteroid oxidoreductase from bovine fetal erythrocytes
Steroids
37
539-553
1981
Bos taurus
Manually annotated by BRENDA team
Hatono-Sato, F.; Shikita, M.
20alpha-hydroxy steroid dehydrogenase of cultured mammalian (HeLa S3) cells
Endocrinol. Jpn.
20
385-390
1973
Homo sapiens
Manually annotated by BRENDA team
Zhang, Y.; Dufort, I.; Rheault, P.; Luu-The, V.
Characterization of a human 20alpha-hydroxysteroid dehydrogenase
J. Mol. Endocrinol.
25
221-228
2000
Homo sapiens, Mammalia
Manually annotated by BRENDA team
Inazu, A.; Sato, K.; Nakayama, T.; Deyashiki, Y.; Hara, A.; Nozawa, Y.
Purification and characterization of a novel dimeric 20alpha-hydroxysteroid dehydrogenase from Tetrahymena pyriformis
Biochem. J.
297
195-200
1994
Tetrahymena pyriformis
Manually annotated by BRENDA team
Hara, A.; Inazu, A.; Deyashiki, Y.; Nozawa, Y.
Substrate specificity and kinetic mechanism of Tetrahymena 20alpha-hydroxysteroid dehydrogenase
Adv. Exp. Med. Biol.
372
249-258
1995
Tetrahymena pyriformis, Tetrahymena thermophila
Manually annotated by BRENDA team
Mao, J.; Duan, R.W.; Zhong, L.; Gibori, G.; Azhar, S.
Expression, purification and characterization of the rat luteal 20alpha-hydroxysteroid dehydrogenase
Endocrinology
138
182-190
1997
Rattus norvegicus
Manually annotated by BRENDA team
Ma, H.; Penning, T.M.
Characterization of homogeneous recombinant rat ovarian 20alpha-hydroxysteroid dehydrogenase: fluorescent properties and inhibition profile
Biochem. J.
341
853-859
1999
Rattus norvegicus
Manually annotated by BRENDA team
Albarracin, C.T.; Parmer, T.G.; Duan, W.R.; Nelson, S.E.; Gibori, G.
Identification of a major prolactin-regulated protein as 20alpha-hydroxysteroid dehydrogenase: coordinate regulation of its activity, protein content, and messenger ribonucleic acid expression
Endocrinology
134
2453-2460
1994
Rattus norvegicus
Manually annotated by BRENDA team
Ma, H.; Penning, T.M.
Conversion of mammalian 3alpha-hydroxysteroid dehydrogenase to 20alpha-hydroxysteroid dehydrogenase using loop chimeras: changing specificity from androgens to progestins
Proc. Natl. Acad. Sci. USA
96
11161-11166
1999
Rattus norvegicus
Manually annotated by BRENDA team
Couture, J.F.; Cantin, L.; Legrand, P.; Luu-The, V.; Labrie, F.; Breton, R.
Expression, crystallization and preliminary X-ray analysis of human and rabbit 20alpha-hydroxysteroid dehydrogenases in complex with NADP(H) and various steroid substrates
Acta Crystallogr. Sect. D
58
135-139
2002
Homo sapiens, Oryctolagus cuniculus
Manually annotated by BRENDA team
Wiebe, J.P.; Lewis, M.J.
Activity and expression of progesterone metabolizing 5alpha-reductase, 20alpha-hydroxysteroid oxidoreductase and 3alpha(beta)-hydroxysteroid oxidoreductases in tumorigenic (MCF-7, MDA-MB-231, T-47D) and nontumorigenic (MCF-10A) human breast cancer cells
BMC Cancer
3
9
2003
Homo sapiens
Manually annotated by BRENDA team
Higaki, Y.; Usami, N.; Shintani, S.; Ishikura, S.; El-Kabbani, O.; Hara, A.
Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone
Chem. Biol. Interact.
143-144
503-513
2003
Homo sapiens
Manually annotated by BRENDA team
Couture, J.F.; Legrand, P.; Cantin, L.; Luu-The, V.; Labrie, F.; Breton, R.
Human 20alpha-hydroxysteroid dehydrogenase: crystallographic and site-directed mutagenesis studies lead to the identification of an alternative binding site for C21-steroids
J. Mol. Biol.
331
593-604
2003
Homo sapiens
Manually annotated by BRENDA team
Hershkovitz, L.; Beuschlein, F.; Klammer, S.; Krup, M.; Weinstein, Y.
Adrenal 20alpha-hydroxysteroid dehydrogenase in the mouse catabolizes progesterone and 11-deoxycorticosterone and is restricted to the X-zone
Endocrinology
148
976-988
2006
Mus musculus, Mus musculus BALB/c
Manually annotated by BRENDA team
Blanchette, S.; Blouin, K.; Richard, C.; Dupont, P.; Luu-The, V.; Tchernof, A.
Expression and activity of 20alpha-hydroxysteroid dehydrogenase (AKR1C1) in abdominal subcutaneous and omental adipose tissue in women
J. Clin. Endocrinol. Metab.
90
264-270
2005
Homo sapiens
Manually annotated by BRENDA team
Brown, K.A.; Boerboom, D.; Bouchard, N.; Dore, M.; Lussier, J.G.; Sirois, J.
Human chorionic gonadotropin-dependent induction of an equine aldo-keto reductase (AKR1C23) with 20alpha-hydroxysteroid dehydrogenase activity during follicular luteinization in vivo
J. Mol. Endocrinol.
36
449-461
2006
Equus caballus, Equus caballus (Q1XAA8)
Manually annotated by BRENDA team
Jayasekara, W.S.; Yonezawa, T.; Ishida, M.; Yamanouchi, K.; Nishihara, M.
Expression and possible role of 20alpha-hydroxysteroid dehydrogenase in the placenta of the goat
J. Reprod. Dev.
51
265-272
2005
Capra hircus
Manually annotated by BRENDA team
Shimada, H.; Miura, K.; Imamura, Y.
Characteristics and inhibition by flavonoids of 20alpha-hydroxysteroid dehydrogenase activity in mouse tissues
Life Sci.
78
2931-2936
2006
Mus musculus
Manually annotated by BRENDA team
Piekorz, R.P.; Gingras, S.; Hoffmeyer, A.; Ihle, J.N.; Weinstein, Y.
Regulation of progesterone levels during pregnancy and parturition by signal transducer and activator of transcription 5 and 20alpha-hydroxysteroid dehydrogenase
Mol. Endocrinol.
19
431-440
2005
Mus musculus
Manually annotated by BRENDA team
Shimada, H.; Ohtaguro, M.; Miura, K.; Imamura, Y.
Inhibitory effects of diesel exhaust components and flavonoids on 20alpha-hydroxysteroid dehydrogenase activity in mouse tissues
J. Enzyme Inhib. Med. Chem.
22
445-449
2007
Mus musculus
Manually annotated by BRENDA team
Nio, J.; Iwanaga, T.
Galectins in the mouse ovary: concomitant expression of galectin-3 and progesterone degradation enzyme (20alpha-HSD) in the corpus luteum
J. Histochem. Cytochem.
55
423-432
2007
Mus musculus, Mus musculus (Q8K023)
Manually annotated by BRENDA team
Ishida, M.; Choi, J.H.; Hirabayashi, K.; Matsuwaki, T.; Suzuki, M.; Yamanouchi, K.; Horai, R.; Sudo, K.; Iwakura, Y.; Nishihara, M.
Reproductive phenotypes in mice with targeted disruption of the 20alpha-hydroxysteroid dehydrogenase gene
J. Reprod. Dev.
53
499-508
2007
Mus musculus
Manually annotated by BRENDA team
Imamura, Y.; Ohtaguro, M.; Shimada, H.
Several distinct enzymes catalyze 20alpha-hydroxysteroid dehydrogenase activity in mouse liver and kidney
J. Steroid Biochem. Mol. Biol.
107
120-126
2007
Mus musculus
Manually annotated by BRENDA team
Dhagat, U.; Carbone, V.; Chung, R.P.; Matsunaga, T.; Endo, S.; Hara, A.; El-Kabbani, O.
A salicylic acid-based analogue discovered from virtual screening as a potent inhibitor of human 20alpha-hydroxysteroid dehydrogenase
Med. Chem.
3
546-550
2007
Homo sapiens
Manually annotated by BRENDA team
Dhagat, U.; Endo, S.; Sumii, R.; Hara, A.; El-Kabbani, O.
Selectivity determinants of inhibitor binding to human 20alpha-hydroxysteroid dehydrogenase: crystal structure of the enzyme in ternary complex with coenzyme and the potent inhibitor 3,5-dichlorosalicylic acid
J. Med. Chem.
51
4844-4848
2008
Homo sapiens, Homo sapiens (Q04828)
Manually annotated by BRENDA team
El-Kabbani, O.; Scammells, P.J.; Gosling, J.; Dhagat, U.; Endo, S.; Matsunaga, T.; Soda, M.; Hara, A.
Structure-guided design, synthesis, and evaluation of salicylic acid-based inhibitors targeting a selectivity pocket in the active site of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1)
J. Med. Chem.
52
3259-3264
2009
Homo sapiens
Manually annotated by BRENDA team
Choi, J.H.; Ishida, M.; Matsuwaki, T.; Yamanouchi, K.; Nishihara, M.
Involvement of 20alpha-hydroxysteroid dehydrogenase in the maintenance of pregnancy in mice
J. Reprod. Dev.
54
408-412
2008
Mus musculus
Manually annotated by BRENDA team
Smuc, T.; Rizner, T.L.
Aberrant pre-receptor regulation of estrogen and progesterone action in endometrial cancer
Mol. Cell. Endocrinol.
301
74-82
2009
Homo sapiens
Manually annotated by BRENDA team
Dhagat, U.; Endo, S.; Soda, M.; Hara, A.; El-Kabbani, O.
Factorizing the role of a critical leucine residue in the binding of substrate to human 20alpha-hydroxysteroid dehydrogenase (AKR1C1): molecular modeling and kinetic studies of the Leu308Val mutant enzyme
Bioorg. Med. Chem. Lett.
20
5274-5276
2010
Homo sapiens, Homo sapiens (Q04828)
Manually annotated by BRENDA team
Stefane, B.; Brozic, P.; Vehovc, M.; Rizner, T.L.; Gobec, S.
New cyclopentane derivatives as inhibitors of steroid metabolizing enzymes AKR1C1 and AKR1C3
Eur. J. Med. Chem.
44
2563-2571
2009
Homo sapiens (Q04828)
Manually annotated by BRENDA team
El-Kabbani, O.; Scammells, P.J.; Day, T.; Dhagat, U.; Endo, S.; Matsunaga, T.; Soda, M.; Hara, A.
Structure-based optimization and biological evaluation of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) salicylic acid-based inhibitors
Eur. J. Med. Chem.
45
5309-5317
2010
Homo sapiens, Homo sapiens (Q04828)
Manually annotated by BRENDA team
Naumann, J.M.; Zoellner, A.; Dragan, C.A.; Messinger, J.; Adam, J.; Bureik, M.
Biotechnological production of 20-alpha-dihydrodydrogesterone at pilot scale
Appl. Biochem. Biotechnol.
165
190-203
2011
Homo sapiens
Manually annotated by BRENDA team
El-Kabbani, O.; Dhagat, U.; Soda, M.; Endo, S.; Matsunaga, T.; Hara, A.
Probing the inhibitor selectivity pocket of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) with X-ray crystallography and site-directed mutagenesis
Bioorg. Med. Chem. Lett.
21
2564-2567
2011
Homo sapiens
Manually annotated by BRENDA team
Naumann, J.M.; Messinger, J.; Bureik, M.
Human 20alpha-hydroxysteroid dehydrogenase (AKR1C1)-dependent biotransformation with recombinant fission yeast Schizosaccharomyces pombe
J. Biotechnol.
150
161-170
2010
Homo sapiens
Manually annotated by BRENDA team
Nanjidsuren, T.; Naidansuren, P.; Park, C.W.; Park, J.J.; Yun, S.J.; Sim, B.W.; Kang, M.H.; Lee, S.R.; Chang, K.T.; Min, K.S.
Expression and localization of the 20alpha-hydroxysteroid dehydrogenase (HSD) enzyme in the reproductive tissues of the cynomolgus monkey Macaca fascicularis
J. Steroid Biochem. Mol. Biol.
127
337-344
2011
Macaca fascicularis
Manually annotated by BRENDA team
Naidansuren, P.; Park, C.W.; Kim, S.H.; Nanjidsuren, T.; Park, J.J.; Yun, S.J.; Sim, B.W.; Hwang, S.; Kang, M.H.; Ryu, B.Y.; Hwang, S.Y.; Yoon, J.T.; Yamanouchi, K.; Min, K.S.
Molecular characterization of bovine placental and ovarian 20alpha-hydroxysteroid dehydrogenase
Reproduction
142
723-731
2011
Bos taurus
Manually annotated by BRENDA team
Kim, S.; Shin, Y.; Kang, M.; Yoon, J.; Min, K.
Gene expression and localization of 20alpha-hydroxysteroid dehydrogenase (HSD) in reproductive tissues during early pregnancy of cattle
Anim. Reprod. Sci.
147
1-9
2014
Bos taurus (D0VDT4)
Manually annotated by BRENDA team
Papp, E.; Balogun, K.; Banko, N.; Mohammadi, H.; Loutfy, M.; Yudin, M.; Shah, R.; Macgillivray, J.; Murphy, K.; Walmsley, S.; Silverman, M.; Serghides, L.
Low prolactin and high 20-alpha-hydroxysteroid dehydrogenase levels contribute to lower progesterone levels in hiv-infected pregnant women exposed to protease inhibitor-based combination antiretroviral therapy
J. Infect. Dis.
213
1532-1540
2016
Homo sapiens
Manually annotated by BRENDA team