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
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
| 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 |
DescriptionCurator'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
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
Sample Use Guides
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
Edited
Sat Dec 16 06:08:22 UTC 2023
by
admin
on
Sat Dec 16 06:08:22 UTC 2023
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| Record UNII |
4G7IHY560Z
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| Record Status |
Validated (UNII)
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| Record Version |
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256737
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4G7IHY560Z
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84051
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DB07702
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1228-72-4
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DTXSID00858947
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17α-Epiestriol
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42156
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