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Literature summary extracted from

  • 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 (2015), Bioorg. Med. Chem., 23, 5433-5451.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.64 (3alpha,5alpha)-3-([(2R,5S)-2,5-dimethyl-4-[2-(trifluoromethyl)benzene-1-sulfonyl]piperazin-1-yl]methyl)-3-hydroxyandrostan-17-one
-
Homo sapiens
1.1.1.64 (3R,5S,5'R,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-(3-methylbutyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,5'R,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,5'R,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyl-5'-(2-methylpropyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,5'R,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,5'S,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-(3-methylbutyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,5'S,8R,9S,10S,13S,14S)-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,5'S,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyl-5'-phenoxytetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(2-phenylethyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(3-phenylpropyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(4-phenylbutyl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(prop-2-en-1-yl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-(prop-2-yn-1-yl)tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(4-phenoxyphenyl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(5-phenoxy-1H-1,2,3-triazol-1-yl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(naphthalen-1-yl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[(naphthalen-2-yl)methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[2-[4-(trifluoromethyl)phenyl]ethyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[4-(trifluoromethyl)benzene-1-sulfonyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[4-(trifluoromethyl)benzoyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[2-(trifluoromethyl)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[3'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[3-(trifluoromethyl)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[4-(trifluoromethoxy)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4'-[[4-(trifluoromethyl)phenyl]methyl]tetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-4'-benzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-4'-[(4-bromophenyl)methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-4'-[([1,1'-biphenyl]-4-yl)methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-4'-[[2,4-bis(trifluoromethyl)phenyl]methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3R,5S,8R,9S,10S,13S,14S)-4'-[[3,5-bis(trifluoromethyl)phenyl]methyl]-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione
-
Homo sapiens
1.1.1.64 (3S)-3,4-dibenzyl-1-oxa-4-azaspiro[5.5]undecan-2-one
-
Homo sapiens
1.1.1.64 (3S)-3-benzyl-1-oxa-4-azaspiro[5.5]undecan-2-one
-
Homo sapiens
1.1.1.64 (3S)-3-benzyl-4-(prop-2-yn-1-yl)-1-oxa-4-azaspiro[5.5]undecan-2-one
-
Homo sapiens
1.1.1.64 (3S)-3-benzyl-4-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-1-oxa-4-azaspiro[5.5]undecan-2-one
-
Homo sapiens
1.1.1.64 (5alpha)-3-hydroxyandrostan-17-one
-
Homo sapiens
1.1.1.64 1-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-3-(morpholin-4-yl)propan-2-yl cyclohexanecarboxylate
-
Homo sapiens
1.1.1.64 canadine
-
Homo sapiens
1.1.1.64 corydaline
-
Homo sapiens
1.1.1.64 corypalmine
-
Homo sapiens
1.1.1.64 methyl (2R)-2-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-4-methylpentanoate
-
Homo sapiens
1.1.1.64 methyl (2R)-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl](phenoxy)acetate
-
Homo sapiens
1.1.1.64 methyl (2S)-2-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]-4-methylpentanoate
-
Homo sapiens
1.1.1.64 methyl (2S)-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl](phenoxy)acetate
-
Homo sapiens
1.1.1.64 methyl [(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2',17-dioxohexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-3,5'-[1,3]oxazolidin]-3'-yl]acetate
-
Homo sapiens
1.1.1.64 additional information design, chemical synthesis and biological evaluation of 3-spiromorpholinone/3-spirocarbamate androsterone derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 3, structure-activity relationship study, overview Homo sapiens
1.1.1.64 scoulerine
-
Homo sapiens
1.1.1.64 Stylopine
-
Homo sapiens
1.1.1.64 tetrahydrocolumbamine
-
Homo sapiens
1.1.1.64 tetrahydroplamatine
-
Homo sapiens

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.1.1.64 microsome
-
Homo sapiens
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.64 testosterone + NADP+ Homo sapiens
-
androstenedione + NADPH + H+
-
r

Organism

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

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.64 LNCaP cell
-
Homo sapiens
-
1.1.1.64 prostate cancer cell
-
Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.64 testosterone + NADP+
-
Homo sapiens androstenedione + NADPH + H+
-
r

Synonyms

EC Number Synonyms Comment Organism
1.1.1.64 17beta-HSD3
-
Homo sapiens
1.1.1.64 17beta-hydroxysteroid dehydrogenase type 3
-
Homo sapiens

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.64 NADP+
-
Homo sapiens
1.1.1.64 NADPH
-
Homo sapiens

General Information

EC Number General Information Comment Organism
1.1.1.64 malfunction enzyme inhibition results in reduced cell proliferation Homo sapiens
1.1.1.64 metabolism enzyme 17beta-HSD3 acts in the last step of the biosynthesis of testosterone Homo sapiens