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Term:
17beta-hydroxy-17-methylestra-4,9,11-trien-3-one (CHEBI:379896)
Annotations: Rat: (411) Mouse: (413) Human: (419) Chinchilla: (0) Bonobo: (0) Dog: (0) Squirrel: (0) Pig: (0)
Parent Terms Term With Siblings Child Terms
3-oxo steroid +     
androgen +   
estrane +   
(13S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol 
(16R)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-16,17-diol 
(1R)-1-ethynyl-1-hydroxy-8-(hydroxymethyl)-9a,11a-dimethyl-2H,3H,3aH,3bH,4H,5H,8H,9H,9bH,10H,11H-cyclopenta[a]phenanthren-7-one 
(1S,3aS,3bR,5aR,9aR,9bR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide 
(1S,7R,9bR)-9b-fluoro-1,9a,11a-trimethyl-2H,3H,3aH,3bH,4H,5H,7H,8H,9H,10H,11H-cyclopenta[a]phenanthrene-1,5,7,10-tetrol 
(1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide 
(1S,9aS,9bR)-9b-fluoro-1-hydroxy-1,9a,11a-trimethyl-2H,3H,3aH,3bH,4H,5H,8H,9H,11H-cyclopenta[a]phenanthrene-7,10-dione 
(1S,9aS,9bR,11aS)-9b-fluoro-1-hydroxy-1,9a,11a-trimethyl-2H,3H,3aH,3bH,4H,5H,8H,9H,11H-cyclopenta[a]phenanthrene-7,10-dione 
(1S,9bR)-9b-fluoro-1,5,10-trihydroxy-1,9a,11a-trimethyl-2H,3H,3aH,3bH,4H,5H,8H,9H,10H,11H-cyclopenta[a]phenanthren-7-one 
(1S,9bR)-9b-fluoro-1,5,10-trihydroxy-1,9a,11a-trimethyl-dodecahydrocyclopenta[a]phenanthren-7-one 
(1S,9bR)-9b-fluoro-1,5-dihydroxy-1,9a,11a-trimethyl-2H,3H,3aH,3bH,4H,5H,8H,9H,11H-cyclopenta[a]phenanthrene-7,10-dione 
(1S,9bR)-9b-fluoro-1-hydroxy-1,9a,11a-trimethyl-2H,3H,3aH,3bH,4H,5H,5aH,6H,8H,9H-cyclopenta[a]phenanthren-7-one 
(25R)-7alpha,26-dihydroxycholest-4-en-3-one 
(3alpha,5alpha,17beta)-17-hydroxyandrostan-3-yl sulfate 
(3beta,5alpha,11beta,17beta)-9-Fluoro-17-methylandrostane-3,11,17-triol 
(3R,5R,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol 
(3S,10R,13S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one 
(8R,9S,13S,14R,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol 
(9bR)-9b-fluoro-5,10-dihydroxy-1,1,9a-trimethyl-2H,3H,3bH,4H,5H,5aH,6H,8H,9H,10H,11H-cyclopenta[a]phenanthren-7-one 
(9R,17S)-9-fluoro-17-hydroxy-10,13,17-trimethyl-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione 
(Z)-11beta,21-Dihydroxypregna-1,4,17(20)-trien-3-one 
1'H-5alpha-Androst-2-eno[3,2-b]indol-17beta-ol 
1-methylestra-1,3,5(10),6-tetraene-3,17beta-diol 
10,13-dimethyl-1,2,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,4,17-trione 
10,13-dimethyl-17-phenyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol 
11-Ketoandrosterone 
11-Ketoetiocholanolone 
11-oxotestosterone 
11alpha,17beta-Dihydroxy-1,4-androstadien-3-one 
11alpha,17beta-Dihydroxy-17-methylandrost-4-en-3-one 
11alpha,17beta-Dihydroxy-17alpha-methylandrosta-1,4-dien-3-one 
11alpha,17beta-Dihydroxy-2alpha,17-dimethylandrost-4-en-3-one 
11alpha,17beta-Dihydroxyandrost-4-en-3-one 
11alpha-Hydroxyandrosta-1,4-diene-3,17-dione 
11beta,17beta-Dihydroxy-12alpha-methylandrost-4-en-3-one 
11beta,17beta-Dihydroxy-17-methyl-5alpha-androstan-3-one 
11beta,17beta-Dihydroxy-17-methylandrost-4-en-3-one 
11beta,17beta-Dihydroxy-17alpha-methylandrosta-1,4-dien-3-one 
11beta,17beta-Dihydroxy-4,17-dimethylandrost-4-en-3-one 
11beta,17beta-Dihydroxy-6alpha,17-dimethylandrost-4-en-3-one 
11beta-hydroxyandrost-4-ene-3,17-dione 
11beta-hydroxytestosterone 
12alpha-Fluoro-11beta,17beta-dihydroxyandrost-4-en-3-one 
12alpha-Fluoro-11beta,17beta-dihydroxyandrosta-1,4-dien-3-one 
14-Hydroxyandrosta-1,4-diene-3,17-dione 
14alpha,17beta-Dihydroxyandrost-4-en-3-one 
15alpha-hydroxyestradiol 
15alpha-hydroxyestrone 
15alpha-hydroxytestosterone 
16-Butyl-3-methoxy-estra-1,3,5(10)-triene-16beta,17beta-diol 
16-Propyl-3-methoxy-estra-1,3,5(10)-triene-16beta,17beta-diol 
16alpha-Fluoro-17alpha-hydroxyandrost-4-en-3-one 
16alpha-Fluoroandrost-4-ene-3,17-dione 
16alpha-hydroxyandrost-4-ene-3,17-dione 
16alpha-hydroxytestosterone  
16beta-Chloro-17beta-hydroxyandrost-4-en-3-one 
16beta-Chloroandrost-4-ene-3,17-dione 
16beta-Fluoroandrost-4-ene-3,17-dione 
16beta-hydroxyestradiol +  
16beta-hydroxyestrone 
16beta-hydroxytestosterone 
17-epiestriol +  
17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione 
17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one 
17-hydroxy-10,13,17-trimethyl-3-oxo-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-2-carboxaldehyde 
17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one 
17-Hydroxy-3-oxo-17alpha-pregna-4,6-diene-21-carboxylic acid 
17-Methylandrost-5-ene-3beta,11beta,17beta-triol 
17-Methylandrosta-2,4-dieno[2,3-d]isoxazol-17beta-ol 
17alpha,2alpha-Dimethyl-17beta-hydroxy-4-androsten-3-one 
17alpha-ethynylestradiol 3-sulfate 
17alpha-Methyl-17beta-hydroxyandrosta-4,6-dien-3-one 
17alpha-Methyl-5alpha-androstane-3alpha,17beta-diol 
17alpha-Methyl-5alpha-androstane-3beta,11beta,17beta-triol 
17beta-(1H-Imidazol-4-yl)androst-5-en-3beta-ol 
17beta-[Bis(2-hydroxyethyl)amino]androst-5-en-3beta-ol 
17beta-Acetamidoandrost-4-en-3-one 
17beta-Carbomethoxyandrost-5-en-3beta-ol 
17beta-estradiol +   
17beta-estradiol 3-benzoate  
17beta-estradiol 3-glucosiduronic acid  
17beta-estradiol 3-O-carboxymethyl ether 
17beta-estradiol 3-sulfate 
17beta-Hydroxy-16alpha-methoxy-androst-4-en-3-one 
17beta-Hydroxy-17-methyl-5alpha-androst-9(11)-en-3-one 
17beta-Hydroxy-17-methylandrost-4-ene-3,11-dione 
17beta-Hydroxy-17-methylandrosta-4,9(11)-dien-3-one 
17beta-hydroxy-17-methylestra-4,9,11-trien-3-one  
A synthetic non-aromatisable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.
17beta-Hydroxy-2,17-dimethyl-5alpha-androst-1-en-3-one 
17beta-Hydroxy-2-methylandrost-1,4-dien-3-one 
17beta-Hydroxy-2alpha,17-dimethyl-4,9(11)-androstadien-3-one 
17beta-hydroxy-2alpha,17-dimethylestr-4-en-3-one 
17beta-hydroxy-2alpha-methylestr-4-en-3-one 
17beta-Hydroxy-3-methoxyestra-1,3,5(10)-trien-16-one 
17beta-Hydroxy-3-methoxyestra-1,3,5(10)-triene-17-carbonitrile 
17beta-Hydroxy-4-methylandrost-4-en-3-one 
17beta-Hydroxy-4-methylestr-4-en-3-one 
17beta-hydroxy-4alpha-methyl-5alpha-androstan-3-one 
17beta-hydroxy-5-androsten-3-one 
17beta-hydroxy-5alpha-androstan-3-one +   
17beta-hydroxy-5alpha-estr-1(10)-en-3-one 
17beta-hydroxy-5beta-androst-1-en-3-one 
17beta-hydroxy-5beta-estran-3-one 
17beta-Hydroxy-6alpha,17-dimethylandrost-4-en-3-one 
17beta-Hydroxy-6alpha-methylandrost-4-en-3-one 
17beta-Hydroxy-6beta-methylandrost-4-en-3-one 
17beta-Hydroxy-7alpha,17-dimethylandrosta-1,4-dien-3-one 
17beta-Hydroxy-7alpha-mercaptoandrost-4-en-3-one 7-propionate 
17beta-Hydroxy-7alpha-methylandrost-1,4-diene-3-one 
17beta-Hydroxy-7alpha-methylandrost-4-en-3-one 
17beta-Hydroxyandrosta-4,9(11)-dien-3-one 
17beta-hydroxyandrostan-3-one +   
17beta-hydroxyestr-5(10)-en-3-one 
17beta-Methoxyandrost-5-ene-3beta,16beta-diol 
17beta-Pyrazol-3-ylandrost-5-en-3beta-ol 
18-hydroxy-5alpha-dihydrotestosterone 
18-hydroxycorticosterone 
19-Chloro-17beta-hydroxyandrost-4-en-3-one 
19-hydroxy-5alpha-dihydrotestosterone 
19-hydroxyandrost-4-ene-3,17-dione 
19-hydroxytestosterone 
19-Norandrostenedione 
19-norandrosterone 
19-Norpregna-4,17(20)-dien-3-one 
19-oxo-5alpha-dihydrotestosterone 
19-oxotestosterone 
1alpha,5alpha-Dimercaptoandrostane-3alpha,17beta-diol 
1alpha-hydroxytestosterone 
1beta-hydroxytestosterone 
2,17beta-Dihydroxy-17-methylandrosta-1,4-dien-3-one 
2-hydroxy-17beta-estradiol +   
2-hydroxy-17beta-estradiol 2-O-(beta-D-glucuronide) 
2-hydroxy-17beta-estradiol 3-O-(beta-D-glucuronide) 
2-hydroxy-17beta-estradiol 3-sulfate 
2-hydroxyestradiol 3-methyl ether 
2-hydroxytestosterone +  
2-methoxy-17beta-estradiol +  
2-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide) 
2alpha-(Hydroxymethyl)-17-methyl-5alpha-androstane-3beta,17beta-diol 
2alpha-(Hydroxymethyl)-5alpha-androstane-3beta,17beta-diol 
2alpha-fluoro-17beta-hydroxyandrost-4-en-3-one 
2alpha-hydroxytestosterone 
2alpha-Methyl-5alpha-androstane-3alpha,17beta-diol 
2alpha-Methyl-5alpha-androstane-3beta,17beta-diol 
3,6-Dimethoxyestra-1,3,5(10),6,8-pentaene-17beta-carboxylic acid methyl ester 
3-(17-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl)propanoic acid 
3-(17-hydroxy-10,13-dimethyl-3-oxo-7-propyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl)propanoic acid 
3-(2-allyloxy)estra-1,3,5(10)-triene-16,17-dione 16-oxime 
3-(allyloxy)estra-1,3,5(10)-triene-16alpha,17beta-diol 
3-(Allyloxy)estra-1,3,5(10)-triene-16beta,17beta-diol 
3-dehydro-4-carboxyzymosterol 
3-dehydroecdysone 
3-Deoxyestradiol 
3-Deoxyestrone  
3-Ethyl-5alpha-androstane-3alpha,17beta-diol 
3-Ethynyl-5alpha-androstane-3beta,17beta-diol 
3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one 
3-Methoxy-16-ethylestra-1,3,5(10)-triene-16beta,17beta-diol 
3-Methoxy-16-octylestra-1,3,5(10)-triene-16beta,17beta-diol 
3-Methoxyestra-1,3,5(10),16-tetraene 
3-methoxyestra-1,3,5(10)-trien-16beta-ol 
3-Methoxyestra-1,3,5(10)-triene-16,17-dione 16-oxime 
3-Methoxyestriol 
3-oxo Delta(7)-steroid +  
3-oxo-5alpha-steroid +   
3-oxo-5beta-steroid +   
3-oxo-Delta(1) steroid +   
3-oxo-Delta(4) steroid +   
3-oxo-Delta(5)-steroid +   
3alpha,11beta-Dihydroxy-5alpha-androstane-17-one 
3alpha,11beta-Dihydroxy-5beta-androstane-17-one 
3alpha-Ethynyl-3-hydroxy-5alpha-androstan-17-one 
3alpha-Hydroxy-2alpha-methyl-5alpha-androstan-17-one 
3beta-Hydroxy-16beta-(hydroxymethyl)-5alpha-androstan-17-one 
3beta-Hydroxy-5-androsten-16-one 
3beta-Hydroxy-5alpha-androstane-7,17-dione 
4,5-dihydrocortisone +   
4-Androstenediol 
4-Chloro-17alpha-methyl-17beta-hydroxy-4-androsten-3-one 
4-hydroxy-17beta-estradiol 3-O-(beta-D-glucuronide) 
4-hydroxy-17beta-estradiol 4-O-(beta-D-glucuronide) 
4-methoxy-17beta-estradiol +   
4-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide) 
4alpha-methyl-3-oxosteroid +  
4alpha-methyl-5alpha-cholest-8-en-3-one 
4beta,5-Epoxy-17beta-hydroxy-5beta-androstan-3-one 
5-Androstene-3beta,16alpha-diol 
5-Androstene-3beta,16beta-diol 
5-Androstenetriol 
5alpha-Androst-1-ene-3,11,17-trione 
5alpha-androst-16-en-3-one 
5alpha-Androstan-3alpha-ol 
5alpha-androstane-3alpha-glcosyl-17beta-diol 
5alpha-androstane-3beta,17beta-diol +  
5alpha-androstane-3beta,6alpha,17beta-triol 
5alpha-androstane-3beta,7alpha,17beta-triol 
5alpha-cholest-8-en-3-one 
5alpha-estrane 
5beta-androstane-3beta,17beta-diol 
5beta-dihydrotestosterone 
5beta-estrane +  
6,7-didehydro-17beta-estradiol 
6,9-difluoro-11-hydroxy-17-(3-hydroxy-2-oxopropyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioic acid S-(fluoromethyl) ester 
6-(Dibromomethylene)-17beta-hydroxyandrost-4-en-3-one 
6-dehydrotestosterone +  
6alpha,17-Dimethyl-5alpha-androstane-3beta,17beta-diol 
6beta,17-Dimethyl-5alpha-androstane-3beta,17beta-diol 
6beta-hydroxyestrone 
6beta-hydroxytestosterone +   
7,8-didehydro-17beta-estradiol 
7alpha -hydroxytestosterone 
7alpha,12alpha,26-trihydroxycholest-4-en-3-one 
7alpha,17beta-Dihydroxy-17alpha-methylandrost-4-en-3-one 
7alpha,17beta-Dihydroxyandrosta-1,4-dien-3-one 
7alpha-hydroxyestradiol 
9-Bromo-17beta-hydroxy-17-methylandrost-4-ene-3,11-dione 
9-Chloro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one 
9-Chloro-17beta-hydroxy-17-methylandrost-4-ene-3,11-dione 
9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one 
9-Fluoro-11beta,17beta-dihydroxy-16alpha-methylandrosta-1,4-dien-3-one 
9-Fluoro-11beta,17beta-dihydroxy-2,17-dimethylandrost-4-en-3-one 
9-Fluoro-11beta-hydroxy-16alpha-methylandrosta-1,4-diene-3,17-dione 
9-Fluoro-11beta-hydroxy-16beta-methylandrosta-1,4-diene-3,17-dione 
9-Fluoro-16alpha-hydroxyandrost-4-ene-3,11,17-trione 
9-Fluoro-17-methyl-11-oxotestosterone 
9-fluoro-17-methyl-5beta-androstane-3alpha,11beta,17beta-triol 
9-Fluoro-17beta-hydroxy-6alpha,17-dimethylandrost-4-ene-3,11-dione 
9-Thiocyanato-androst-4-ene-3,11,17-trione 
adrenosterone  
Allylestrenol  
anabolic androgenic steroid +   
andrastin D +  
androisoxazole 
androst-4-ene-3,17-dione +   
Androst-5-ene-3beta,17beta,19-triol 
androst-5-ene-3beta,17beta-diol  
androst-5-ene-3beta,7alpha,17beta-triol 
Androsta-4,9(11)-diene-3,17-dione 
androstane-3,17-dione +   
androstane-3alpha,17beta-diol +  
androsterone +   
benzoic acid (17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl) ester 
benzoic acid [(13S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] ester 
Bolasterone 
boldenone  
Bothermon 
C18-steroid +  
calotropone 
calusterone 
campest-4-en-3-one 
clostebol 
cloxotestosterone 
dafachronic acids +  
danazol  
dehydroepiandrosterone +   
Delta(1)-dihydrotestosterone 
desogestrel  
dienogest  
Dimethisterone 
epiandrosterone +  
epietiocholanolone 
Epimestrol 
epitestosterone 17-O-(beta-D-glucuronide) 
equilin +   
estetrol 
Estra-1,3,5(10),16-tetraen-3-ol benzoate 
estra-1,3,5(10)-trien-3-ol  
Estra-1,3,5(10)-triene-2,17beta-diol 
estra-1,3,5(10)-triene-3,16beta-diol  
Estra-1,3,5(10)-triene-3,17beta-diol 3-phosphate 
Estra-1,3,5-(10)-trien-17-one-3-oxyacetic acid 
estradiol +   
estramustine +   
estrane derivative +  
estriol +   
estriol 16-O-(beta-D-glucuronide)  
estriol 3-O-(beta-D-glucuronide)  
estrone +   
estrone 3-sulfate  
ethinylestradiol sulfonate 
ethisterone 
ethylestrenol  
ethynodiol +   
etonogestrel  
finasteride  
fluoxymesterone  
formebolone 
fulvestrant  
Furazabol 
glucosyl-6beta-hydroxytestosterone 
guggulsterone  
Hydroxystenozole 
kidjoranin-3-O-alpha-diginopyranosyl-(1->4)-beta-cymaropyranoside 
kidjoranin-3-O-beta-digitoxopyranoside 
levonorgestrel  
LSM-1379 
LSM-5093 
LSM-5126 
LSM-5853 
LSM-6384 
LSM-6713 
Lynestrenol 
mestranol  
Methandriol 
methenolone 
metholone +  
methyltestosterone  
mibolerone  
mifepristone  
mytatrienediol 
nandrolone +   
nandrolone phenpropionate  
norelgestromin  
norethisterone +   
Oranabol 
otophylloside B 
oxandrolone  
oxymetholone +   
promegestone  
promestriene 
quinbolone 
quinestradol 
RU 58668  
stanozolol  
Stenbolone 
testosterone +   
testosterone 17-glucosiduronic acid  
testosterone enanthate  
tibolone  
tiomesterone 
trilostane  
zhankuic acid A +  
zhankuic acid A methyl ester 
zymosterol intermediate 2 

Synonyms
Related Synonyms: 17-beta-Hydroxy-17-methylestra-4,9,11-trien-3-one ;   17-methyloestra-4,9,11-trien-3-one,17beta-ol ;   17alpha-Methyltrienolone ;   Formula=C19H24O2 ;   InChI=1S/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/m1/s1 ;   InChIKey=CCCIJQPRIXGQOE-XWSJACJDSA-N ;   Methyltrienolone ;   R1881 ;   R1881 (synthetic androgen) ;   SMILES=[H][C@@]12CCC3=CC(=O)CCC3=C1C=C[C@@]1(C)[C@@]2([H])CC[C@]1(C)O ;   metribolona ;   metribolone ;   metribolonum
Alternate IDs: CHEBI:45313 ;   CHEBI:59645
Xrefs: Beilstein:2626053 "Beilstein" ;   CAS:965-93-5 "ChemIDplus" ;   CAS:965-93-5 "KEGG COMPOUND" ;   DrugBank:DB02998 ;   KEGG:C14257
Xref Mesh: MESH:D015741
Xrefs: PDBeChem:R18 ;   PMID:17077481 "Europe PMC" ;   Patent:NL6401555

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.