CHEBI:27974 - estriol

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ChEBI Name estriol
ChEBI ID CHEBI:27974
Definition A 3-hydroxy steroid that is estra-1,3,5(10)-trien-3-ol substituted by additional hydroxy groups at positions 16 and 17 (16α,17β-stereoisomer).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42467, CHEBI:4869, CHEBI:23969
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Formula C18H24O3
Net Charge 0
Average Mass 288.38140
Monoisotopic Mass 288.17254
InChI InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
InChIKey PROQIPRRNZUXQM-ZXXIGWHRSA-N
SMILES [H][C@]12CC[C@]3(C)[C@@H](O)[C@H](O)C[C@@]3([H])[C@]1([H])CCc1cc(O)ccc21
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): estrogen
A hormone that stimulates or controls the development and maintenance of female sex characteristics in mammals by binding to oestrogen receptors. The oestrogens are named for their importance in the oestrous cycle. The oestrogens that occur naturally in the body, notably estrone, estradiol, estriol, and estetrol are steroids. Other compounds with oestrogenic activity are produced by plants (phytoestrogens) and fungi (mycoestrogens); synthetic compounds with oestrogenic activity are known as xenoestrogens.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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ChEBI Ontology
Outgoing estriol (CHEBI:27974) has parent hydride estrane (CHEBI:23966)
estriol (CHEBI:27974) has role estrogen (CHEBI:50114)
estriol (CHEBI:27974) has role human metabolite (CHEBI:77746)
estriol (CHEBI:27974) has role human xenobiotic metabolite (CHEBI:76967)
estriol (CHEBI:27974) has role mouse metabolite (CHEBI:75771)
estriol (CHEBI:27974) is a 16α-hydroxy steroid (CHEBI:16799)
estriol (CHEBI:27974) is a 17β-hydroxy steroid (CHEBI:35343)
estriol (CHEBI:27974) is a 3-hydroxy steroid (CHEBI:36834)
Incoming 3-(allyloxy)estra-1,3,5(10)-triene-16α,17β-diol (CHEBI:79756) has functional parent estriol (CHEBI:27974)
6-ketoestriol (CHEBI:145763) has functional parent estriol (CHEBI:27974)
estriol 16-O-(β-D-glucuronide) (CHEBI:766) has functional parent estriol (CHEBI:27974)
estriol 3-O-(β-D-glucuronide) (CHEBI:45869) has functional parent estriol (CHEBI:27974)
IUPAC Name
estra-1,3,5(10)-triene-3,16α,17β-triol
Synonyms Sources
(16α,17β)-estra-1,3,5(10)-triene-3,16,17-triol NIST Chemistry WebBook
1,3,5(10)-Estratriene-3,16-alpha,17beta-triol KEGG COMPOUND
16α,17β-estriol UniProt
16α-hydroxyestradiol NIST Chemistry WebBook
3,16α,17β-trihydroxy-Δ1,3,5-estratriene NIST Chemistry WebBook
Estriol KEGG COMPOUND
ESTRIOL PDBeChem
oestriol NIST Chemistry WebBook
Östriol ChEBI
trihydroxyestrin NIST Chemistry WebBook
Brand Names Sources
Deuslon-A Deprecated term DrugBank
Estriel DrugBank
Manual Xrefs Databases
1907 VSDB
3187 DrugCentral
C05141 KEGG COMPOUND
D00185 KEGG DRUG
DB04573 DrugBank
ESL PDBeChem
Estriol Wikipedia
ESTRIOL MetaCyc
HMDB0000153 HMDB
LMST02010003 LIPID MAPS
LSM-2368 LINCS
View more database links
Registry Numbers Types Sources
2508172 Reaxys Registry Number Reaxys
50-27-1 CAS Registry Number KEGG COMPOUND
50-27-1 CAS Registry Number ChemIDplus
50-27-1 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11133265 PubMed citation Europe PMC
23777262 PubMed citation Europe PMC
9373313 PubMed citation Europe PMC
Last Modified
20 January 2020