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:CB9181225, eMolecules:477779, ZINC000003814360
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Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production of sebum and body hair composition. The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues including the prostate gland, seminal vesicles, epididymides, skin, hair follicles, liver, and brain. This enzyme mediates reduction of the C4-5 double bond of testosterone. DHT may also be synthesized from progesterone and 17α-hydroxyprogesterone via the androgen backdoor pathway in the absence of testosterone. Relative to testosterone, DHT is considerably more potent as an agonist of the androgen receptor (AR). In addition to its role as a natural hormone, DHT has been used as a medication, for instance in the treatment of low testosterone levels in men; for information on DHT as a medication, see the androstanolone article.
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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).
View more via ChEBI Ontology
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
Sakhri S, Gooren LJ (2007)
Safety aspects of androgen treatment with 5alpha-dihydrotestosterone.
Andrologia 39, 216-222 [PubMed:18076420]
[show Abstract]
Putnam SK, Sato S, Riolo JV, Hull EM (2005)
Effects of testosterone metabolites on copulation, medial preoptic dopamine, and NOS-immunoreactivity in castrated male rats.
Hormones and behavior 47, 513-522 [PubMed:15811352]
[show Abstract]
Edinger KL, Lee B, Frye CA (2004)
Mnemonic effects of testosterone and its 5alpha-reduced metabolites in the conditioned fear and inhibitory avoidance tasks.
Pharmacology, biochemistry, and behavior 78, 559-568 [PubMed:15251265]
[show Abstract]
Last Modified
22 August 2017