CHEBI:16330 - 17β-hydroxy-5α-androstan-3-one

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ChEBI Name 17β-hydroxy-5α-androstan-3-one
ChEBI ID CHEBI:16330
ChEBI ASCII Name 17beta-hydroxy-5alpha-androstan-3-one
Definition A 17β-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with α-configuration at position 5.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:793, CHEBI:11342, CHEBI:41876, CHEBI:11341, CHEBI:19175
Supplier Information ChemicalBook:CB9258118, ZINC000003875484
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Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia. It is taken by mouth. Side effects of fluoxymesterone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause liver damage and cardiovascular side effects like high blood pressure. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization. Fluoxymesterone was first described in 1956 and was introduced for medical use in 1957. In addition to its medical use, fluoxymesterone is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.
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Formula C19H30O2
Net Charge 0
Average Mass 290.44030
Monoisotopic Mass 290.22458
InChI InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
InChIKey NVKAWKQGWWIWPM-ABEVXSGRSA-N
SMILES [H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CCC(=O)C2
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Daphnia magna (NCBI:txid35525) See: Changes in the Metabolic Elimination Profile of Testosterone Following Exposure of the Crustacean Daphnia magna to TributyltinGerald A. LeBlanc and James B. McLachlanEcotoxicology and Environmental Safety 45, 296-303 (2000)
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): androgen
A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors.
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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ChEBI Ontology
Outgoing 17β-hydroxy-5α-androstan-3-one (CHEBI:16330) has parent hydride 5α-androstane (CHEBI:28859)
17β-hydroxy-5α-androstan-3-one (CHEBI:16330) has role Daphnia magna metabolite (CHEBI:83056)
17β-hydroxy-5α-androstan-3-one (CHEBI:16330) has role androgen (CHEBI:50113)
17β-hydroxy-5α-androstan-3-one (CHEBI:16330) has role human metabolite (CHEBI:77746)
17β-hydroxy-5α-androstan-3-one (CHEBI:16330) has role mouse metabolite (CHEBI:75771)
17β-hydroxy-5α-androstan-3-one (CHEBI:16330) is a 17β-hydroxy steroid (CHEBI:35343)
17β-hydroxy-5α-androstan-3-one (CHEBI:16330) is a 17β-hydroxyandrostan-3-one (CHEBI:85278)
17β-hydroxy-5α-androstan-3-one (CHEBI:16330) is a 3-oxo-5α-steroid (CHEBI:13601)
Incoming 18-hydroxy-5α-dihydrotestosterone (CHEBI:137037) has functional parent 17β-hydroxy-5α-androstan-3-one (CHEBI:16330)
19-hydroxy-5α-dihydrotestosterone (CHEBI:137031) has functional parent 17β-hydroxy-5α-androstan-3-one (CHEBI:16330)
19-oxo-5α-dihydrotestosterone (CHEBI:137032) has functional parent 17β-hydroxy-5α-androstan-3-one (CHEBI:16330)
5α-dihydrotestosterone 17-O-(β-D-glucuronide) (CHEBI:89417) has functional parent 17β-hydroxy-5α-androstan-3-one (CHEBI:16330)
5α-dihydrotestosterone 17-O-[β-D-glucuronosyl-(1→2)-glucuronide] (CHEBI:137856) has functional parent 17β-hydroxy-5α-androstan-3-one (CHEBI:16330)
5α-dihydrotestosterone sulfate (CHEBI:138026) has functional parent 17β-hydroxy-5α-androstan-3-one (CHEBI:16330)
IUPAC Name
17β-hydroxy-5α-androstan-3-one
INNs Sources
androstanolona ChemIDplus
androstanolone WHO MedNet
androstanolone ChemIDplus
androstanolonum ChemIDplus
Synonyms Sources
17beta-hydroxy-5alpha-androstan-3-one ChEBI
17beta-Hydroxy-5alpha-androstan-3-one KEGG COMPOUND
17β-hydroxy-5α-androstan-3-one UniProt
17beta-hydroxyandrostan-3-one ChEBI
17beta-Hydroxyandrostan-3-one KEGG COMPOUND
17beta-Hydroxyandrostan-3-one KEGG COMPOUND
4,5α-dihydrotestosterone ChEBI
5α-DHT ChEBI
5alpha-dihydrotestosterone ChEBI
5alpha-Dihydrotestosterone KEGG COMPOUND
Androstanolone KEGG COMPOUND
DHT PDBeChem
Dihydrotestosteron ChEBI
DIHYDROTESTOSTERONE PDBeChem
dihydrotestostérone ChEBI
Stanolone NIST Chemistry WebBook
Manual Xrefs Databases
17-BETA-HYDROXY-5ALPHA-ANDROSTAN-3-O MetaCyc
3927 DrugCentral
C03917 KEGG COMPOUND
D07456 KEGG DRUG
DB02901 DrugBank
DHT PDBeChem
Dihydrotestosterone Wikipedia
HMDB0002961 HMDB
LMST02020042 LIPID MAPS
View more database links
Registry Numbers Types Sources
521-18-6 CAS Registry Number KEGG COMPOUND
521-18-6 CAS Registry Number NIST Chemistry WebBook
521-18-6 CAS Registry Number ChemIDplus
Citations Types Sources
15251265 PubMed citation Europe PMC
15811352 PubMed citation Europe PMC
18076420 PubMed citation Europe PMC
Last Modified
22 August 2017