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:

mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

anti-HIV agent An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.

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).

antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.

analgesic An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.

Applications:

antirheumatic drug A drug used to treat rheumatoid arthritis.

hypoglycemic agent A drug which lowers the blood glucose level.

antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.

vasodilator agent A drug used to cause dilation of the blood vessels.

geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

appetite enhancer A drug which increases appetite.

antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.

antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	dehydroepiandrosterone (CHEBI:28689) has role analgesic (CHEBI:35480)
	dehydroepiandrosterone (CHEBI:28689) has role androgen (CHEBI:50113)
	dehydroepiandrosterone (CHEBI:28689) has role anti-HIV agent (CHEBI:64946)
	dehydroepiandrosterone (CHEBI:28689) has role antidepressant (CHEBI:35469)
	dehydroepiandrosterone (CHEBI:28689) has role antimalarial (CHEBI:38068)
	dehydroepiandrosterone (CHEBI:28689) has role antineoplastic agent (CHEBI:35610)
	dehydroepiandrosterone (CHEBI:28689) has role antirheumatic drug (CHEBI:35842)
	dehydroepiandrosterone (CHEBI:28689) has role appetite enhancer (CHEBI:50779)
	dehydroepiandrosterone (CHEBI:28689) has role geroprotector (CHEBI:176497)
	dehydroepiandrosterone (CHEBI:28689) has role human metabolite (CHEBI:77746)
	dehydroepiandrosterone (CHEBI:28689) has role hypoglycemic agent (CHEBI:35526)
	dehydroepiandrosterone (CHEBI:28689) has role mouse metabolite (CHEBI:75771)
	dehydroepiandrosterone (CHEBI:28689) has role vasodilator agent (CHEBI:35620)
	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
3-BETA-HYDROXY-5-ANDROSTEN-17-ONE	PDBeChem
3beta-hydroxyandrost-5-en-17-one	ChEBI
3beta-Hydroxyandrost-5-en-17-one	KEGG COMPOUND
3beta-Hydroxyandrost-5-en-17-one	KEGG COMPOUND
Androst-5-en-3.alpha.-ol-17-one	ChEMBL
Biolaif	ChEMBL

Brand Names	Source
Enzymatic therapy	ChEMBL
Intrarosa	ChemIDplus
Natrol dhea	ChEMBL

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

Manual Xrefs	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

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

Citations