CHEBI:2710 - androst-5-ene-3β,17β-diol

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ChEBI Name androst-5-ene-3β,17β-diol
ChEBI ID CHEBI:2710
ChEBI ASCII Name androst-5-ene-3beta,17beta-diol
Definition A 3β-hydroxy-Δ5-steroid that is 3β-hydroxyandrost-5-ene carrying an additional hydroxy group at position 17β.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB4742825, eMolecules:713322, eMolecules:29549802, ZINC000003814414
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Formula C19H30O2
Net Charge 0
Average Mass 290.447
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/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
InChIKey QADHLRWLCPCEKT-LOVVWNRFSA-N
SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
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.
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).
Application(s): radiation protective agent
Any compound that is able to protect normal cells from the damage caused by radiation therapy.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing androst-5-ene-3β,17β-diol (CHEBI:2710) has parent hydride androstane (CHEBI:35509)
androst-5-ene-3β,17β-diol (CHEBI:2710) has role androgen (CHEBI:50113)
androst-5-ene-3β,17β-diol (CHEBI:2710) has role human metabolite (CHEBI:77746)
androst-5-ene-3β,17β-diol (CHEBI:2710) has role mouse metabolite (CHEBI:75771)
androst-5-ene-3β,17β-diol (CHEBI:2710) has role radiation protective agent (CHEBI:66987)
androst-5-ene-3β,17β-diol (CHEBI:2710) is a 17β-hydroxy steroid (CHEBI:35343)
androst-5-ene-3β,17β-diol (CHEBI:2710) is a 3β-hydroxy-Δ5-steroid (CHEBI:1722)
Incoming androstenediol 3-sulfate(1−) (CHEBI:190287) has functional parent androst-5-ene-3β,17β-diol (CHEBI:2710)
IUPAC Name
androst-5-ene-3β,17β-diol
Synonyms Sources
(3β,17β)-androst-5-ene-3,17-diol ChemIDplus
3beta,17beta-Dihydroxy-5-androstene KEGG COMPOUND
3β,17β-dihydroxyandrost-5-ene ChemIDplus
3beta,17beta-Dihydroxyandrost-5-ene KEGG COMPOUND
5-androstenediol ChEBI
androst-5-en-3β,17β-diol UniProt
Androst-5-ene-3beta,17beta-diol KEGG COMPOUND
androst-5-enediol ChemIDplus
Androstenediol KEGG COMPOUND
hermaphrodiol ChemIDplus
Manual Xrefs Databases
10188 ChemSpider
214 DrugCentral
B81 PDBeChem
C04295 KEGG COMPOUND
D00179 KEGG DRUG
DB01524 DrugBank
FDB023228 FooDB
HMDB0003818 HMDB
LMST02020005 LIPID MAPS
WO9963973 Patent
View more database links
Registry Number Type Source
521-17-5 CAS Registry Number ChemIDplus
Citations
Wu T, Liu W, Fan T, Zhong H, Zhou H, Guo W, Zhu X (2020)
5-Androstenediol prevents radiation injury in mice by promoting NF-κB signaling and inhibiting AIM2 inflammasome activation.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 121, 109597 [PubMed:31726369]
[show Abstract]
Plaza F, Gabler F, Romero C, Vantman D, Valladares L, Vega M (2010)
The conversion of dehydroepiandrosterone into androst-5-ene-3beta,17beta-diol (androstenediol) is increased in endometria from untreated women with polycystic ovarian syndrome.
Steroids 75, 810-817 [PubMed:20620158]
[show Abstract]
Marwah A, Gomez FE, Marwah P, Ntambi JM, Fox BG, Lardy H (2006)
Redox reactions of dehydroepiandrosterone and its metabolites in differentiating 3T3-L1 adipocytes: A liquid chromatographic-mass spectrometric study.
Archives of biochemistry and biophysics 456, 1-7 [PubMed:17078923]
[show Abstract]
Padgett DA, MacCallum RC, Loria RM, Sheridan JF (2000)
Androstenediol-induced restoration of responsiveness to influenza vaccination in mice.
The journals of gerontology. Series A, Biological sciences and medical sciences 55, B418-24 [PubMed:10995038]
[show Abstract]
Ball WJ, Kasturi R, Dey P, Tabet M, O'Donnell S, Hudson D, Fishwild D (1999)
Isolation and characterization of human monoclonal antibodies to digoxin.
Journal of immunology (Baltimore, Md. : 1950) 163, 2291-2298 [PubMed:10438974]
[show Abstract]
Last Modified
17 January 2023