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1.1.1.64: testosterone 17beta-dehydrogenase (NADP+)

This is an abbreviated version!
For detailed information about testosterone 17beta-dehydrogenase (NADP+), go to the full flat file.

Word Map on EC 1.1.1.64

Reaction

testosterone
+
NADP+
=
androstenedione
+
NADPH
+
H+

Synonyms

17-ketoreductase, 17beta-HSD, 17beta-HSD 3, 17beta-HSD type 3, 17beta-HSD type 5, 17beta-HSD-3, 17beta-HSD1, 17beta-HSD3, 17beta-HSD4, 17beta-HSD5, 17beta-hydroxysteroid dehydrogenase, 17beta-hydroxysteroid dehydrogenase 3, 17beta-hydroxysteroid dehydrogenase type 3, 17beta-hydroxysteroid dehydrogenase type 5, 17beta-hydroxysteroid dehydrogenases type 3, 17betaHSD3, 3beta-hydroxysteroid dehydrogenase type 3, AKR1C3, HSD17B3, More, NADP-dependent testosterone-17beta-oxidoreductase, type 3 17beta-HSD, type 3 17beta-hydroxysteroid dehydrogenase, type 5 17beta-hydroxysteroid dehydrogenase, type 5 beta-hydroxysteroid dehydrogenase

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.64 testosterone 17beta-dehydrogenase (NADP+)

Reference

Reference on EC 1.1.1.64 - testosterone 17beta-dehydrogenase (NADP+)

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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hara, A.; Nakayama, T.; Nakagawa, M.; Inoue, Y.; Tanabe, H.; Sawada, H.
Kinetic and stereochemical studies on reaction mechanism of mouse liver 17beta-hydroxysteroid dehydrogenases
J. Biochem.
102
1585-1592
1987
Mus musculus
Manually annotated by BRENDA team
Villee, C.A.; Spencer, J.M.
Some properties of the pyridine nucleotide-specific 17beta-hydroxy steroid dehydrogenases of guinea pig liver
J. Biol. Chem.
235
3615-3619
1960
Cavia porcellus
Manually annotated by BRENDA team
Andersson, S.; Geissler, W.M.; Wu, L.; Davis, D.L.; Grumbach, M.M.; New, M.I.; Schwarz, H.P.; Blethen, S.L.; Mendoca.B.B.; Bloise, W.; Witchel, S.F.; Cutler, G.B.; Griffin, J.E.; Wilson, J.D.; Russell, D.W.
Molecular genetics and pathophysiology of 17beta-hydroxysteroid dehydrogenase 3 deficiency
J. Clin. Endocrinol.
81
130-136
1996
Homo sapiens
Manually annotated by BRENDA team
Baker, M.E.
Unusual evolution of 11beta- and 17beta-hydroxysteroid dehydrogenases
BioEssays
18
63-70
1995
Homo sapiens
Manually annotated by BRENDA team
Geissler, W.M.; Davis, D.L.; Wu, L.; Bradshaw, K.D.; Patel, S.; Mendoca, B.B.; Elliston, K.O.; Wilson, J.D.; Russell, D.W.; Andersson, S.
Male pseudohermaphroditism caused by mutations of testicular 17beta-hydroxysteroid dehydrogenase 3
Nature Genet.
7
34-39
1994
Homo sapiens
Manually annotated by BRENDA team
Inano, H.; Tamaoki, B.
Testicular 17beta-hydroxysteroid dehydrogenas: molecular properties and reaction mechanism
Steroids
48
1-26
1986
Oryctolagus cuniculus, Ovis aries, Rattus norvegicus, Sus scrofa
Manually annotated by BRENDA team
Hara, A.; Hayashibara, M.; Nakayama, T.; Hasabe, K.; Usui, s.; Sawada, H.
Guinea-pig liver testosterone 17beta-dehydrogenase (NADP+) and aldehyde reductase exhibit benzene dihydrodiol dehydrogenase activity
Biochem. J.
225
177-181
1985
Cavia porcellus
Manually annotated by BRENDA team
Inano, H.; Tamaoki, B.; Hamana, K.; Nakagawa, H.
Amino acid composition and immunochemical properties of porcine testicular 17beta-hydroxysteroid dehydrogenase
J. Steroid Biochem.
13
287-295
1980
Sus scrofa
Manually annotated by BRENDA team
Kageura, E.; Toki, S.
Purification and properties of a new testosterone 17beta-dehydrogenase (NADP+) from guinea-pig liver
Biochem. J.
163
401-407
1977
Cavia porcellus
Manually annotated by BRENDA team
Inano, H.; Tamaoki, B.
Relationship between steroids and pyridine nucleotides in the oxido-reduction catalyzed by the 17beta-hydroxysteroid dehydrogenase purified from the porcine testicular microsomal fraction
Eur. J. Biochem.
53
319-326
1975
Sus scrofa
Manually annotated by BRENDA team
Tamaoki, B-i.; Inano, H.
Testicular 17beta-hydroxysteroid dehydrogenase: its distribution, purification and properties
J. Steroid Biochem.
6
361-363
1975
Rattus norvegicus, Sus scrofa
Manually annotated by BRENDA team
Inano, H.; Tamaoki, B.
Purificatition and properties of NADP-dependent 17beta-hydroxysteoid dehydrogenase solubilized from porcine-testicular microsomal fraction
Eur. J. Biochem.
44
13-23
1974
Sus scrofa
Manually annotated by BRENDA team
Oshima, H.; Ochiai, K.
On testicular 17beta-hydroxysteroid oxidoreductase product activation of testosterone formation from androstendione in vitro
Biochim. Biophys. Acta
306
227-236
1973
Oryctolagus cuniculus, Homo sapiens
Manually annotated by BRENDA team
Endahl, G.L.; Kochakian, C.D.; Hamm, D.
Separation of a triphosphopyridine nucleotide-specific from a diphosphopyridine nucleotide-specific 17beta-hydroxy-(testosterone)dehydrogenase of guinea-pig liver
J. Biol. Chem.
235
2792-2796
1960
Cavia porcellus
Manually annotated by BRENDA team
Khan, N.; Sharma, K.K.; Andersson, S.; Auchus, R.J.
Human 17beta-hydroxysteroid dehydrogenases types 1, 2, and 3 catalyze bi-directional equilibrium reactions, rather than unidirectional metabolism, in HEK-293 cells
Arch. Biochem. Biophys.
429
50-59
2004
Homo sapiens
Manually annotated by BRENDA team
McKeever, B.M.; Hawkins, B.K.; Geissler, W.M.; Wu, L.; Sheridan, R.P.; Mosley, R.T.; Andersson, S.
Amino acid substitution of arginine 80 in 17beta-hydroxysteroid dehydrogenase type 3 and its effect on NADPH cofactor binding and oxidation/reduction kinetics
Biochim. Biophys. Acta
1601
29-37
2002
Homo sapiens
Manually annotated by BRENDA team
Poirier, D.
Inhibitors of 17beta-hydroxysteroid dehydrogenases
Curr. Med. Chem.
10
453-477
2003
Canis lupus familiaris, Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
le Lain, R.; Barrell, K.J.; Saeed, G.S.; Nicholls, P.J.; Simons, C.; Kirby, A.; Smith, H.J.
Some coumarins and triphenylethene derivatives as inhibitors of human testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD type 3): further studies with tamoxifen on the rat testes microsomal enzyme
J. Enzyme Inhib. Med. Chem.
17
93-100
2002
Homo sapiens
Manually annotated by BRENDA team
Lota, R.K.; Dhanani, S.; Owen, C.P.; Ahmed, S.
Synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a series of 4-hydroxyphenyl ketones as potential inhibitors of 17beta-hydroxysteroid dehydrogenase type 3 (17beta-HSD3)
Bioorg. Med. Chem. Lett.
16
4519-4522
2006
Rattus norvegicus
Manually annotated by BRENDA team
Tchedam Ngatcha, B.; Luu-The, V.; Labrie, F.; Poirier, D.
Androsterone 3alpha-ether-3beta-substituted and androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: chemical synthesis and structure-activity relationship
J. Med. Chem.
48
5257-5268
2005
Homo sapiens
Manually annotated by BRENDA team
Mindnich, R.; Haller, F.; Halbach, F.; Moeller, G.; Hrabe de Angelis, M.; Adamski, J.
Androgen metabolism via 17beta-hydroxysteroid dehydrogenase type 3 in mammalian and non-mammalian vertebrates: comparison of the human and the zebrafish enzyme
J. Mol. Endocrinol.
35
305-316
2005
Danio rerio, Homo sapiens
Manually annotated by BRENDA team
Brozic, P.; Golob, B.; Gomboc, N.; Rizner, T.L.; Gobec, S.
Cinnamic acids as new inhibitors of 17beta-hydroxysteroid dehydrogenase type 5 (AKR1C3)
Mol. Cell. Endocrinol.
248
233-235
2006
Homo sapiens
Manually annotated by BRENDA team
Moeller, G.; Adamski, J.
Multifunctionality of human 17beta-hydroxysteroid dehydrogenases
Mol. Cell. Endocrinol.
248
47-55
2006
Homo sapiens
Manually annotated by BRENDA team
Parthasarathy, C.; Balasubramanian, K.
Effects of corticosterone deficiency and its replacement on Leydig cell steroidogenesis
J. Cell. Biochem.
104
1671-1683
2008
Rattus norvegicus (O54939)
Manually annotated by BRENDA team
Hu, G.X.; Zhou, H.Y.; Li, X.W.; Chen, B.B.; Xiao, Y.C.; Lian, Q.Q.; Liang, G.; Kim, H.H.; Zheng, Z.Q.; Hardy, D.O.; Ge, R.S.
The (+)- and (-)-gossypols potently inhibit both 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase 3 in human and rat testes
J. Steroid Biochem. Mol. Biol.
115
14-19
2009
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Day, J.M.; Tutill, H.J.; Foster, P.A.; Bailey, H.V.; Heaton, W.B.; Sharland, C.M.; Vicker, N.; Potter, B.V.; Purohit, A.; Reed, M.J.
Development of hormone-dependent prostate cancer models for the evaluation of inhibitors of 17beta-hydroxysteroid dehydrogenase type 3
Mol. Cell. Endocrinol.
301
251-258
2009
Homo sapiens
Manually annotated by BRENDA team
Nakamura, Y.; Hornsby, P.; Casson, P.; Morimoto, R.; Satoh, F.; Xing, Y.; Kennedy, M.; Sasano, H.; Rainey, W.
Type 5 17ß-hydroxysteroid dehydrogenase (AKR1C3) contributes to testosterone production in the adrenal reticularis
J. Clin. Endocrinol. Metab.
94
2192-2198
2009
Homo sapiens
Manually annotated by BRENDA team
Jackson, V.J.; Yosaatmadja, Y.; Flanagan, J.U.; Squire, C.J.
Structure of AKR1C3 with 3-phenoxybenzoic acid bound
Acta Crystallogr. Sect. F
68
409-413
2012
Homo sapiens (P42330)
Manually annotated by BRENDA team
Adeniji, A.O.; Twenter, B.M.; Byrns, M.C.; Jin, Y.; Winkler, J.D.; Penning, T.M.
Discovery of substituted 3-(phenylamino)benzoic acids as potent and selective inhibitors of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3)
Bioorg. Med. Chem. Lett.
21
1464-1468
2011
Homo sapiens (P42330)
Manually annotated by BRENDA team
Chen, M.; Adeniji, A.O.; Twenter, B.M.; Winkler, J.D.; Christianson, D.W.; Penning, T.M.
Crystal structures of AKR1C3 containing an N-(aryl)amino-benzoate inhibitor and a bifunctional AKR1C3 inhibitor and androgen receptor antagonist. Therapeutic leads for castrate resistant prostate cancer
Bioorg. Med. Chem. Lett.
22
3492-3497
2012
Homo sapiens (P42330)
Manually annotated by BRENDA team
Harada, K.; Kubo, H.; Tanaka, A.; Nishioka, K.
Identification of oxazolidinediones and thiazolidinediones as potent 17beta-hydroxysteroid dehydrogenase type 3 inhibitors
Bioorg. Med. Chem. Lett.
22
504-507
2012
Homo sapiens (P37058)
Manually annotated by BRENDA team
Sinreih, M.; Sosic, I.; Beranic, N.; Turk, S.; Adeniji, A.O.; Penning, T.M.; Rizner, T.L.; Gobec, S.
N-Benzoyl anthranilic acid derivatives as selective inhibitors of aldo-keto reductase AKR1C3
Bioorg. Med. Chem. Lett.
22
5948-5951
2012
Homo sapiens (P42330)
Manually annotated by BRENDA team
Maltais, R.; Fournier, M.A.; Poirier, D.
Development of 3-substituted-androsterone derivatives as potent inhibitors of 17beta-hydroxysteroid dehydrogenase type 3
Bioorg. Med. Chem.
19
4652-4668
2011
Homo sapiens (P37058)
Manually annotated by BRENDA team
Harada, K.; Kubo, H.; Abe, J.; Haneta, M.; Conception, A.; Inoue, S.; Okada, S.; Nishioka, K.
Discovery of potent and orally bioavailable 17beta-hydroxysteroid dehydrogenase type 3 inhibitors
Bioorg. Med. Chem.
20
3242-3254
2012
Homo sapiens (P37058), Rattus norvegicus
Manually annotated by BRENDA team
Yuan, K.; Zhao, B.; Li, X.W.; Hu, G.X.; Su, Y.; Chu, Y.; Akingbemi, B.T.; Lian, Q.Q.; Ge, R.S.
Effects of phthalates on 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase 3 activities in human and rat testes
Chem. Biol. Interact.
195
180-188
2012
Rattus norvegicus, Homo sapiens (P37058)
Manually annotated by BRENDA team
Matsunaga, T.; Hojo, A.; Yamane, Y.; Endo, S.; El-Kabbani, O.; Hara, A.
Pathophysiological roles of aldo-keto reductases (AKR1C1 and AKR1C3) in development of cisplatin resistance in human colon cancers
Chem. Biol. Interact.
202
234-242
2013
Homo sapiens (P42330)
Manually annotated by BRENDA team
Legeza, B.; Balazs, Z.; Nashev, L.G.; Odermatt, A.
The microsomal enzyme 17beta-hydroxysteroid dehydrogenase 3 faces the cytoplasm and uses NADPH generated by glucose-6-phosphate dehydrogenase
Endocrinology
154
205-213
2013
Homo sapiens (P37058)
Manually annotated by BRENDA team
Heinrich, D.M.; Flanagan, J.U.; Jamieson, S.M.; Silva, S.; Rigoreau, L.J.; Trivier, E.; Raynham, T.; Turnbull, A.P.; Denny, W.A.
Synthesis and structure-activity relationships for 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3
Eur. J. Med. Chem.
62
738-744
2013
Homo sapiens (P42330)
Manually annotated by BRENDA team
Gazvoda, M.; Beranic, N.; Turk, S.; Burja, B.; Kocevar, M.; Rizner, T.L.; Gobec, S.; Polanc, S.
2,3-diarylpropenoic acids as selective non-steroidal inhibitors of type-5 17?-hydroxysteroid dehydrogenase (AKR1C3)
Eur. J. Med. Chem.
62
89-97
2013
Homo sapiens (P42330)
Manually annotated by BRENDA team
Zakharov, V.; Lin, H.K.; Azzarello, J.; McMeekin, S.; Moore, K.N.; Penning, T.M.; Fung, K.M.
Suppressed expression of type 2 3alpha/type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3) in endometrial hyperplasia and carcinoma
Int. J. Clin. Exp. Pathol.
3
608-617
2010
Homo sapiens (P42330)
Manually annotated by BRENDA team
Miller, V.L.; Lin, H.K.; Murugan, P.; Fan, M.; Penning, T.M.; Brame, L.S.; Yang, Q.; Fung, K.M.
Aldo-keto reductase family 1 member C3 (AKR1C3) is expressed in adenocarcinoma and squamous cell carcinoma but not small cell carcinoma
Int. J. Clin. Exp. Pathol.
5
278-289
2012
Homo sapiens
Manually annotated by BRENDA team
Brozic, P.; Turk, S.; Adeniji, A.O.; Konc, J.; Janezic, D.; Penning, T.M.; Lanisnik Rizner, T.; Gobec, S.
Selective inhibitors of aldo-keto reductases AKR1C1 and AKR1C3 discovered by virtual screening of a fragment library
J. Med. Chem.
55
7417-7424
2012
Homo sapiens (P42330)
Manually annotated by BRENDA team
Byrns, M.C.; Mindnich, R.; Duan, L.; Penning, T.M.
Overexpression of aldo-keto reductase 1C3 (AKR1C3) in LNCaP cells diverts androgen metabolism towards testosterone resulting in resistance to the 5alpha-reductase inhibitor finasteride
J. Steroid Biochem. Mol. Biol.
130
7-15
2012
Homo sapiens (P42330)
Manually annotated by BRENDA team
Latif, S.A.; Shen, M.; Ge, R.S.; Sottas, C.M.; Hardy, M.P.; Morris, D.J.
Role of 11beta-OH-C(19) and C(21) steroids in the coupling of 11beta-HSD1 and 17beta-HSD3 in regulation of testosterone biosynthesis in rat Leydig cells
Steroids
76
682-689
2011
Rattus norvegicus (O54939)
Manually annotated by BRENDA team
Amano, Y.; Yamaguchi, T.; Niimi, T.; Sakashita, H.
Structures of complexes of type 5 17beta-hydroxysteroid dehydrogenase with structurally diverse inhibitors: insights into the conformational changes upon inhibitor binding
Acta Crystallogr. Sect. D
71
918-927
2015
Homo sapiens (P42330)
Manually annotated by BRENDA team
Djigoue, G.B.; Kenmogne, L.C.; Roy, J.; Poirier, D.
Synthesis of 3-spiromorpholinone androsterone derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 3
Bioorg. Med. Chem. Lett.
23
6360-6362
2013
Rattus norvegicus
Manually annotated by BRENDA team
Djigoue, G.B.; Kenmogne, L.C.; Roy, J.; Maltais, R.; Poirier, D.
Design, chemical synthesis and biological evaluation of 3-spiromorpholinone/3-spirocarbamate androsterone derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 3
Bioorg. Med. Chem.
23
5433-5451
2015
Homo sapiens
Manually annotated by BRENDA team
Skarydova, L.; Hofman, J.; Chlebek, J.; Havrankova, J.; Kosanova, K.; Skarka, A.; Hostalkova, A.; Plucha, T.; Cahlikova, L.; Wsol, V.
Isoquinoline alkaloids as a novel type of AKR1C3 inhibitors
J. Steroid Biochem. Mol. Biol.
143
250-258
2014
Homo sapiens (P42330)
Manually annotated by BRENDA team
Roy, J.; Fournier, M.A.; Maltais, R.; Kenmogne, L.C.; Poirier, D.
Reprint of in vitro and in vivo evaluation of a 3beta-androsterone derivative as inhibitor of 17beta-hydroxysteroid dehydrogenase type 3
J. Steroid Biochem. Mol. Biol.
153
170-178
2015
Rattus norvegicus (O54939), Homo sapiens (P37058), Rattus norvegicus Sprague-Dawley (O54939)
Manually annotated by BRENDA team
Cheng, Y.; Yang, Y.; Wu, Y.; Wang, W.; Xiao, L.; Zhang, Y.; Tang, J.; Huang, Y.D.; Zhang, S.; Xiang, Q.
The curcumin derivative, H10, suppresses hormone-dependent prostate cancer by inhibiting 17beta-hydroxysteroid dehydrogenase type 3
Front. Pharmacol.
11
637
2020
Homo sapiens (P37058)
Manually annotated by BRENDA team
Yazawa, T.; Imamichi, Y.; Uwada, J.; Sekiguchi, T.; Mikami, D.; Kitano, T.; Ida, T.; Sato, T.; Nemoto, T.; Nagata, S.; Islam Khan, M.R.; Takahashi, S.; Ushikubi, F.; Suzuki, N.; Umezawa, A.; Taniguchi, T.
Evaluation of 17beta-hydroxysteroid dehydrogenase activity using androgen receptor-mediated transactivation
J. Steroid Biochem. Mol. Biol.
196
105493
2020
Homo sapiens
Manually annotated by BRENDA team
Ning, X.; Yang, Y.; Deng, H.; Zhang, Q.; Huang, Y.; Su, Z.; Fu, Y.; Xiang, Q.; Zhang, S.
Development of 17beta-hydroxysteroid dehydrogenase type 3 as a target in hormone-dependent prostate cancer therapy
Steroids
121
10-16
2017
Homo sapiens (P37058)
Manually annotated by BRENDA team