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Literature summary extracted from

  • 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 (2005), J. Med. Chem., 48, 5257-5268.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.1.1.51 overexpression in HEK-293 cells Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.51 3alpha-alkylated androsterone derivatives 17-88% inhibition at 0.003 mM, overview Homo sapiens
1.1.1.51 3alpha-ether-3beta-substituted androsterone derivatives diverse derivatives, IC50: 70-760 nM, overview Homo sapiens
1.1.1.51 3beta-alkylated androsterone derivatives IC50: 57-147 nM Homo sapiens
1.1.1.51 3beta-phenylethyl-3alpha-methyl-O-androsterone IC50: 73 nM Homo sapiens
1.1.1.51 3beta-phenylethyl-androsterone IC50: 99 nM Homo sapiens
1.1.1.51 3beta-phenylmethyl-androsterone IC50: 57 nM Homo sapiens
1.1.1.51 3beta-substituted androsterone derivatives IC50: 57-147 nM Homo sapiens
1.1.1.51 additional information synthesis, inhibitory potency, and in vivo effects of the diverse inhibitor derivatives, detailed overview Homo sapiens
1.1.1.64 3-(17'-oxo-5'alpha-androstan-3'alpha-oxy)propanoic acid 0.003 mM, 48% inhibition Homo sapiens
1.1.1.64 3alpha,3beta-O-(1'-oxo-1',3'-propanediyloxy)-5alpha-androstan-17-one 0.003 mM, 53% inhibition Homo sapiens
1.1.1.64 3alpha-(2'-hydroxypropanoxy)-5alpha-androstan-17-one 0.003 mM, 89% inhibition Homo sapiens
1.1.1.64 3alpha-(3'-bromopropanoxy)-5alpha-androstan-17-one 0.003 mM, 93% inhibition Homo sapiens
1.1.1.64 3alpha-(3'-hydroxypropanoxy)-5alpha-androstan-17-one 0.003 mM, 86% inhibition Homo sapiens
1.1.1.64 3alpha-(prop-2'-enoxy)-5alpha-androstan-17-one 0.003 mM, 95% inhibition Homo sapiens
1.1.1.64 3alpha-ethoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one 0.003 mM, 92% inhibition, IC50: 352 nM Homo sapiens
1.1.1.64 3alpha-ethoxy-5alpha-androstan-17-one 0.003 mM, 95% inhibition Homo sapiens
1.1.1.64 3alpha-hexanoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one 0.003 mM, 28% inhibition Homo sapiens
1.1.1.64 3alpha-hexanoxy-5alpha-androstan-17-one 0.003 mM, 92% inhibition Homo sapiens
1.1.1.64 3alpha-hydroxy-3'-phenyl-5alpha-androstan-17-one 0.003 mM, 95% inhibition, IC50: 81 nM Homo sapiens
1.1.1.64 3alpha-hydroxy-3beta-(3'-hydroxypropyl)-5alpha-androstan-17-one 0.003 mM, 74% inhibition Homo sapiens
1.1.1.64 3alpha-hydroxy-3beta-(prop-2'-enyl)-5alpha-androstan-17-one 0.003 mM, 76% inhibition Homo sapiens
1.1.1.64 3alpha-hydroxy-3beta-methyl-5alpha-androstan-17-one 0.003 mM, 93% inhibition Homo sapiens
1.1.1.64 3alpha-hydroxy-3beta-octyl-5alpha-androstan-17-one 0.003 mM, 92% inhibition, IC50: 147 nM Homo sapiens
1.1.1.64 3alpha-hydroxy-3beta-phenylethyl-5alpha-androstan-17-one 0.003 mM, 93% inhibition, IC50: 99 nM Homo sapiens
1.1.1.64 3alpha-hydroxy-3beta-phenylmethyl-5alpha-androstan-17-one 0.003 mM, 94% inhibition, IC50: 57 nM Homo sapiens
1.1.1.64 3alpha-hydroxy-3beta-phenylpropyl-5alpha-androstan-17-one 0.003 mM, 97% inhibition Homo sapiens
1.1.1.64 3alpha-hydroxy-3beta-propyl-5alpha-androstan-17-one 0.003 mM, 94% inhibition, IC50: 67 nM Homo sapiens
1.1.1.64 3alpha-hydroxy-3beta-vinyl-5alpha-androstan-17-one 0.003 mM, 94% inhibition Homo sapiens
1.1.1.64 3alpha-methoxy-3beta-(2'-phenylethyl)-5alpha-androstan-17-one 0.003 mM, 95% inhibition, IC50: 73 nM Homo sapiens
1.1.1.64 3alpha-methoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one 0.003 mM, 93% inhibition, IC50: 154 nM Homo sapiens
1.1.1.64 3alpha-methoxy-5alpha-androstan-17-one 0.003 mM, 94% inhibition Homo sapiens
1.1.1.64 3alpha-O-(spirotetrahydrofuran-2-yl)-5alpha-androstan-17-one 0.003 mM, 94% inhibition Homo sapiens
1.1.1.64 3alpha-propanoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one 0.003 mM, 87% inhibition Homo sapiens
1.1.1.64 3alpha-propanoxy-5alpha-androstan-17-one 0.003 mM, 93% inhibition Homo sapiens
1.1.1.64 3beta,3alpha-O-(1'-oxo-1',3'-propanediyloxy)-5alpha-androstan-17-one 0.003 mM, 93% inhibition Homo sapiens
1.1.1.64 3beta-(2'-cyclohexylethyl)-3alpha-methoxy-5alpha-androstan-17-one 0.003 mM, 88% inhibition, IC50: 354 nM Homo sapiens
1.1.1.64 3beta-cyclohexyl-3alpha-hydroxy-5alpha-androstan-17-one 0.003 mM, 95% inhibition, IC50: 97 nM Homo sapiens
1.1.1.64 3beta-cyclohexylethyl-3alpha-hydroxy-5alpha-androstan-17-one 0.003 mM, 93% inhibition, IC50: 60 nM Homo sapiens
1.1.1.64 3beta-cyclohexylmethyl-3alpha-hydroxy-5alpha-androstan-17-one 0.003 mM, 95% inhibition, IC50: 87 nM Homo sapiens
1.1.1.64 3beta-dodecyl-3alpha-hydroxy-5alpha-androstan-17-one 0.003 mM, 77% inhibition Homo sapiens
1.1.1.64 3beta-hydroxy-3alpha-(3'-hydroxypropyl)-5alpha-androstan-17-one 0.003 mM, 17% inhibition Homo sapiens
1.1.1.64 3beta-hydroxy-3alpha-(prop-2'-enyl)-5alpha-androstan-17-one 0.003 mM, 36% inhibition Homo sapiens
1.1.1.64 3beta-hydroxy-3alpha-methyl-5alpha-androstan-17-one 0.003 mM, 16% inhibition Homo sapiens
1.1.1.64 3beta-hydroxy-3alpha-phenyl-5alpha-androstan-17-one 0.003 mM, 39% inhibition Homo sapiens
1.1.1.64 3beta-hydroxy-3alpha-phenylmethyl-5alpha-androstan-17-one 0.003 mM, 39% inhibition Homo sapiens
1.1.1.64 3beta-hydroxy-3alpha-propyl-5alpha-androstan-17-one 0.003 mM, 33% inhibition Homo sapiens
1.1.1.64 3beta-n-butyl-3alpha-hydroxy-5alpha-androstan-17-one 0.003 mM, 92% inhibition, IC50: 116 nM Homo sapiens
1.1.1.64 3beta-n-hexyl-3alpha-hydroxy-5alpha-androstan-17-one 0.003 mM, 95% inhibition, IC50: 100 nM Homo sapiens
1.1.1.64 3beta-s-butyl-3alpha-hydroxy-5alpha-androstan-17-one 0.003 mM, 90% inhibition, IC50: 73 nM Homo sapiens
1.1.1.64 3beta-tert-butyl-3alpha-hydroxy-5alpha-androstan-17-one 0.003 mM, 93% inhibition, IC50: 142 nM Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.51 androst-4-ene-3,17-dione + NADPH Homo sapiens
-
 testosterone + NADP+
-
 ?
1.1.1.64 androstenedione + NADPH + H+ Homo sapiens the enzyme is involved in biosynthesis of testosterone testosterone + NADP+
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.51 Homo sapiens
-
-
-
1.1.1.64 Homo sapiens
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.51 HEK-293 cell low enzyme expression level Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.51 androst-4-ene-3,17-dione + NADPH
-
 Homo sapiens testosterone + NADP+
-
 ?
1.1.1.64 androstenedione + NADPH + H+
-
 Homo sapiens testosterone + NADP+
-
 ?
1.1.1.64 androstenedione + NADPH + H+ the enzyme is involved in biosynthesis of testosterone Homo sapiens testosterone + NADP+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.1.1.51 type 17beta-HSD
-
 Homo sapiens
1.1.1.51 type 3 17beta-hydroxysteroid dehydrogenase
-
 Homo sapiens
1.1.1.64 type 3 17beta-hydroxysteroid dehydrogenase
-
 Homo sapiens

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.51 NADPH
-
 Homo sapiens
1.1.1.64 NADPH
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.51 0.000057
-
 IC50: 57 nM Homo sapiens 3beta-phenylmethyl-androsterone
1.1.1.51 0.000057 0.000147 IC50: 57-147 nM Homo sapiens 3beta-substituted androsterone derivatives
1.1.1.51 0.000057 0.000147 IC50: 57-147 nM Homo sapiens 3beta-alkylated androsterone derivatives
1.1.1.51 0.00007 0.00076 diverse derivatives, IC50: 70-760 nM, overview Homo sapiens 3alpha-ether-3beta-substituted androsterone derivatives
1.1.1.51 0.000073
-
 IC50: 73 nM Homo sapiens 3beta-phenylethyl-3alpha-methyl-O-androsterone
1.1.1.51 0.000099
-
 IC50: 99 nM Homo sapiens 3beta-phenylethyl-androsterone
1.1.1.64 0.000057
-
 0.003 mM, 94% inhibition, IC50: 57 nM Homo sapiens 3alpha-hydroxy-3beta-phenylmethyl-5alpha-androstan-17-one
1.1.1.64 0.00006
-
 0.003 mM, 93% inhibition, IC50: 60 nM Homo sapiens 3beta-cyclohexylethyl-3alpha-hydroxy-5alpha-androstan-17-one
1.1.1.64 0.000067
-
 0.003 mM, 94% inhibition, IC50: 67 nM Homo sapiens 3alpha-hydroxy-3beta-propyl-5alpha-androstan-17-one
1.1.1.64 0.000073
-
 0.003 mM, 90% inhibition, IC50: 73 nM Homo sapiens 3beta-s-butyl-3alpha-hydroxy-5alpha-androstan-17-one
1.1.1.64 0.000073
-
 0.003 mM, 95% inhibition, IC50: 73 nM Homo sapiens 3alpha-methoxy-3beta-(2'-phenylethyl)-5alpha-androstan-17-one
1.1.1.64 0.000081
-
 0.003 mM, 95% inhibition, IC50: 81 nM Homo sapiens 3alpha-hydroxy-3'-phenyl-5alpha-androstan-17-one
1.1.1.64 0.000087
-
 0.003 mM, 95% inhibition, IC50: 87 nM Homo sapiens 3beta-cyclohexylmethyl-3alpha-hydroxy-5alpha-androstan-17-one
1.1.1.64 0.000097
-
 0.003 mM, 95% inhibition, IC50: 97 nM Homo sapiens 3beta-cyclohexyl-3alpha-hydroxy-5alpha-androstan-17-one
1.1.1.64 0.000099
-
 0.003 mM, 93% inhibition, IC50: 99 nM Homo sapiens 3alpha-hydroxy-3beta-phenylethyl-5alpha-androstan-17-one
1.1.1.64 0.0001
-
 0.003 mM, 95% inhibition, IC50: 100 nM Homo sapiens 3beta-n-hexyl-3alpha-hydroxy-5alpha-androstan-17-one
1.1.1.64 0.000116
-
 0.003 mM, 92% inhibition, IC50: 116 nM Homo sapiens 3beta-n-butyl-3alpha-hydroxy-5alpha-androstan-17-one
1.1.1.64 0.000142
-
 0.003 mM, 93% inhibition, IC50: 142 nM Homo sapiens 3beta-tert-butyl-3alpha-hydroxy-5alpha-androstan-17-one
1.1.1.64 0.000147
-
 0.003 mM, 92% inhibition, IC50: 147 nM Homo sapiens 3alpha-hydroxy-3beta-octyl-5alpha-androstan-17-one
1.1.1.64 0.000154
-
 0.003 mM, 93% inhibition, IC50: 154 nM Homo sapiens 3alpha-methoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
1.1.1.64 0.000352
-
 0.003 mM, 92% inhibition, IC50: 352 nM Homo sapiens 3alpha-ethoxy-3beta-(phenylmethyl)-5alpha-androstan-17-one
1.1.1.64 0.000354
-
 0.003 mM, 88% inhibition, IC50: 354 nM Homo sapiens 3beta-(2'-cyclohexylethyl)-3alpha-methoxy-5alpha-androstan-17-one