dehydroepiandrosterone (CHEBI:28689)

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CHEBI:28689 - dehydroepiandrosterone

ChEBI ID	CHEBI:28689
ChEBI Name	dehydroepiandrosterone
Stars
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.
Secondary ChEBI IDs	CHEBI:1723, CHEBI:11911, CHEBI:20246, CHEBI:40738, CHEBI:86953
Last Modified	24 March 2022
Downloads	Molfile

Formula	C19H28O2
Net Charge	0
Average Mass	288.431
Monoisotopic Mass	288.20893
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]
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

Wikipedia

Species of Metabolite	Component	Source	Comments
Homo sapiens (ncbitaxon:9606)	-	DOI (10.1038/nbt.2488)
Mus musculus (ncbitaxon:10090)	-	PubMed (19425150)	Source: BioModels - MODEL1507180067

Roles Classification

Biological Roles:

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).

androgen A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors.

ChEBI Ontology

Outgoing Relation(s)
	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 Relation(s)
	16α-hydroxydehydroepiandrosterone 3-sulfate (CHEBI:87774) has functional parent dehydroepiandrosterone (CHEBI:28689)
	3β-(2-diethylaminoethoxy)androst-5-en-17-one (CHEBI:190402) has functional parent dehydroepiandrosterone (CHEBI:28689)
	7-ketodehydroepiandrosterone (CHEBI:183808) has functional parent dehydroepiandrosterone (CHEBI:28689)
	7α-hydroxydehydroepiandrosterone (CHEBI:81471) has functional parent dehydroepiandrosterone (CHEBI:28689)
	7β-hydroxydehydroepiandrosterone (CHEBI:183368) has functional parent dehydroepiandrosterone (CHEBI:28689)
	dehydroepiandrosterone 3-β-D-glucoside (CHEBI:145051) 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	Source
3beta-Hydroxyandrost-5-en-17-one	KEGG COMPOUND
Dehydroepiandrosterone	KEGG COMPOUND
Dehydroisoandrosterone	KEGG COMPOUND
DHA	KEGG COMPOUND
DHEA	KEGG COMPOUND
3beta-hydroxyandrost-5-en-17-one	ChEBI

Brand Name	Source
Intrarosa	ChemIDplus

UniProt Name	Source
3β-hydroxyandrost-5-en-17-one	UniProt

Manual Xrefs	Databases
C01227	KEGG COMPOUND
AND	PDBeChem
LMST02020021	LIPID MAPS
DB01708	DrugBank
3-BETA-HYDROXYANDROST-5-EN-17-ONE	MetaCyc
Dehydroepiandrosterone	Wikipedia
HMDB0000077	HMDB
D08409	KEGG DRUG
795	DrugCentral

Registry Numbers	Sources
Reaxys:2058110	Reaxys
CAS:53-43-0	KEGG COMPOUND
CAS:53-43-0	ChemIDplus

Citations