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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 of 17.ALPHA.-ESTRIOL

SMILES

[H][C@@]12C[C@@H](O)[C@@H](O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4

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
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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Sat Dec 16 06:08:22 GMT 2023
Edited
by admin
on Sat Dec 16 06:08:22 GMT 2023
Record UNII
4G7IHY560Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
17.ALPHA.-ESTRIOL
Common 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
NSC-84051
Code English
Code System Code Type Description
PUBCHEM
256737
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
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FDA UNII
4G7IHY560Z
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
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NSC
84051
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
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DRUG BANK
DB07702
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
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CAS
1228-72-4
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
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EPA CompTox
DTXSID00858947
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
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WIKIPEDIA
17α-Epiestriol
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
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CHEBI
42156
Created by admin on Sat Dec 16 06:08:22 GMT 2023 , Edited by admin on Sat Dec 16 06:08:22 GMT 2023
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