CHEBI:28689 - dehydroepiandrosterone

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ChEBI Name dehydroepiandrosterone
ChEBI ID CHEBI:28689
Definition An androstanoid that is androst-5-ene substituted by a β-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40738, CHEBI:1723, CHEBI:20246, CHEBI:11911, CHEBI:86953
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Formula C19H28O2
Net Charge 0
Average Mass 288.42440
Monoisotopic Mass 288.209
InChI InChI=1S/C19H28O2/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/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1
InChIKey FMGSKLZLMKYGDP-USOAJAOKSA-N
SMILES [H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(=O)CC[C@@]21[H]
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:9606) 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.
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 dehydroepiandrosterone (CHEBI:28689) has role androgen (CHEBI:50113)
dehydroepiandrosterone (CHEBI:28689) has role human metabolite (CHEBI:77746)
dehydroepiandrosterone (CHEBI:28689) has role mouse metabolite (CHEBI:75771)
dehydroepiandrosterone (CHEBI:28689) is a 17-oxo steroid (CHEBI:19168)
dehydroepiandrosterone (CHEBI:28689) is a 3β-hydroxy-Δ5-steroid (CHEBI:1722)
dehydroepiandrosterone (CHEBI:28689) is a androstanoid (CHEBI:50402)
Incoming 16α-hydroxydehydroepiandrosterone 3-sulfate (CHEBI:87774) has functional parent dehydroepiandrosterone (CHEBI:28689)
dehydroepiandrosterone 7-O-(carboxymethyl)oxime (CHEBI:62935) has functional parent dehydroepiandrosterone (CHEBI:28689)
dehydroepiandrosterone sulfate (CHEBI:16814) has functional parent dehydroepiandrosterone (CHEBI:28689)
dehydroisoandrosterone 3-glucuronide (CHEBI:68834) has functional parent dehydroepiandrosterone (CHEBI:28689)
prasterone sodium sulfate (CHEBI:32148) has functional parent dehydroepiandrosterone (CHEBI:28689)
IUPAC Name
3β-hydroxyandrost-5-en-17-one
Synonyms Sources
3-BETA-HYDROXY-5-ANDROSTEN-17-ONE PDBeChem
3beta-hydroxyandrost-5-en-17-one ChEBI
3beta-Hydroxyandrost-5-en-17-one KEGG COMPOUND
3β-hydroxyandrost-5-en-17-one UniProt
3beta-Hydroxyandrost-5-en-17-one KEGG COMPOUND
Dehydroepiandrosterone KEGG COMPOUND
Dehydroisoandrosterone KEGG COMPOUND
DHA KEGG COMPOUND
DHEA KEGG COMPOUND
Prasterone ChemIDplus
Brand Name Source
Intrarosa ChemIDplus
Database Links Databases
3-BETA-HYDROXYANDROST-5-EN-17-ONE MetaCyc
795 DrugCentral
AND PDBeChem
C01227 KEGG COMPOUND
D08409 KEGG DRUG
DB01708 DrugBank
Dehydroepiandrosterone Wikipedia
HMDB0000077 HMDB
LMST02020021 LIPID MAPS
View more database links
Registry Numbers Types Sources
2058110 Reaxys Registry Number Reaxys
53-43-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14662261 PubMed citation Europe PMC
18634257 PubMed citation Europe PMC
24256992 PubMed citation Europe PMC
24424045 PubMed citation Europe PMC
Last Modified
25 April 2017