17.ALPHA.-ESTRIOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H24O3
Molecular Weight	288.3814
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(O)=C4)[C@@H]1C[C@@H](O)[C@H]2O

InChI

InChIKey=PROQIPRRNZUXQM-PNVOZDDCSA-N

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

HIDE SMILES / InChI

Molecular Formula	C18H24O3
Molecular Weight	288.3814
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.hmdb.ca/metabolites/HMDB0000356
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23288867 | https://www.ncbi.nlm.nih.gov/pubmed/12547825 | https://www.ncbi.nlm.nih.gov/pubmed/9658195

17α-Epiestriol (17-epiestriol, 16α-hydroxy-17α-estradiol or estra-1,3,5(10)-triene-3,16α,17α-triol) is the 17α-epimer of estriol, a minor hydroxylated estradiol metabolite and a selective estrogen receptor (ER) beta agonist. 17α-Epiestriol is described as a relatively weak estrogen, which is in accordance with its relatively low affinity for the ERα. 17α-Epiestriol has been found to be approximately 400-fold more potent than estradiol in inhibiting tumor necrosis factor α (TNFα)-induced vascular cell adhesion molecule 1 (VCAM-1) expression in vitro.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor beta 113 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9658195	Agonist 2752
UDP-glucuronosyltransferase 2B7 4 Target ID: CHEMBL4370 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23288867	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Regiospecificity and stereospecificity of human UDP-glucuronosyltransferases in the glucuronidation of estriol, 16-epiestriol, 17-epiestriol, and 13-epiestradiol.	2013-03	23288867

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Human umbilical vein endothelial cells (HUVEC) was used for activity evaluation. Human umbilical vein endothelial cells were preincubated with either 17-epiestriol (10, 30, 100, 300 pM and 1, 3, 10 nM) various concentrations for 48 h, and TNFalpha (10 ng/ml) was added to the culture media for the last 4 h. Following this, the cells were collected and total RNA was extracted. RNA was loaded on 1% agarose-formaldehyde gel, electrophoresed, and visualized under UV light after ethidium bromide staining.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:35:45 GMT 2025` Edited by `admin` on `Mon Mar 31 21:35:45 GMT 2025`
Record UNII	4G7IHY560Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

17.ALPHA.-ESTRIOL

Common Name

English

NSC-84051

Preferred Name

English

17-EPIESTRIOL

Common Name

English

ESTRA-1,3,5(10)-TRIENE-3,16,17-TRIOL, (16.ALPHA.,17.ALPHA.)-

Systematic Name

English

ESTRA-1,3,5(10)-TRIENE-3,16.ALPHA.,17.ALPHA.-TRIOL

Systematic Name

English

16.ALPHA.,17.ALPHA.-ESTRIOL

Common Name

English

16.ALPHA.-HYDROXY-17.ALPHA.-ESTRADIOL

Common Name

English

Code System Code Type Description

PUBCHEM

256737