CHEBI:42156 - 17-epiestriol

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ChEBI Name 17-epiestriol
ChEBI ID CHEBI:42156
Definition A 16α-hydroxy steroid that is estriol in which the hydroxy group at position 17 has been epimersied from β- to α- configuration. It is a metabolite of estradiol and a selective estrogen receptor beta (ER-β) agonist.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H24O3
Net Charge 0
Average Mass 288.382
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-PNVOZDDCSA-N
SMILES C12=CC=C(C=C1CC[C@@]3([C@@]2(CC[C@]4([C@]3(C[C@H]([C@H]4O)O)[H])C)[H])[H])O
Roles Classification
Biological Role(s): estrogen receptor agonist
An agonist at the estrogen receptor.
human urinary metabolite
Any metabolite (endogenous or exogenous) found in human urine samples.
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.
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ChEBI Ontology
Outgoing 17-epiestriol (CHEBI:42156) has parent hydride estrane (CHEBI:23966)
17-epiestriol (CHEBI:42156) has role estrogen (CHEBI:50114)
17-epiestriol (CHEBI:42156) has role estrogen receptor agonist (CHEBI:63951)
17-epiestriol (CHEBI:42156) has role human urinary metabolite (CHEBI:84087)
17-epiestriol (CHEBI:42156) is a 16α-hydroxy steroid (CHEBI:16799)
17-epiestriol (CHEBI:42156) is a 17α-hydroxy steroid (CHEBI:35342)
17-epiestriol (CHEBI:42156) is a 3-hydroxy steroid (CHEBI:36834)
Incoming 17-epiestriol 16-O-(β-D-glucuronide) (CHEBI:137706) has functional parent 17-epiestriol (CHEBI:42156)
17-epiestriol 17-O-(β-D-glucuronide) (CHEBI:137702) has functional parent 17-epiestriol (CHEBI:42156)
17-epiestriol 3-O-(β-D-glucuronide) (CHEBI:137701) has functional parent 17-epiestriol (CHEBI:42156)
IUPAC Name
estra-1(10),2,4-triene-3,16α,17α-triol
Synonyms Sources
(16α,17α)-estra-1(10),2,4-triene-3,16,17-triol IUPAC
(8R,9S,13S,14S,16R,17S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,16,17-triol IUPAC
1,3,5(10)-estratriene-3,16α,17α-triol ChEBI
16α,17α-estriol UniProt
16α-hydroxy-17α-estradiol ChEBI
17-epiestriol LIPID MAPS
17α-estriol ChemIDplus
3,16α,17α-trihydroxy-1,3,5(10)-estratriene ChEBI
Manual Xrefs Databases
17-epiestriol Wikipedia
E3O PDBeChem
HMDB0000356 HMDB
LMST02010049 LIPID MAPS
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Registry Numbers Types Sources
1228-72-4 CAS Registry Number ChemIDplus
2622737 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12547825 PubMed citation Europe PMC
23288867 PubMed citation Europe PMC
26063478 PubMed citation Europe PMC
26104910 PubMed citation Europe PMC
26180245 PubMed citation Europe PMC
26460631 PubMed citation Europe PMC
28072767 PubMed citation Europe PMC
Last Modified
10 July 2017