Structure Database (LMSD)
Common Name
Estradiol-17alpha
Systematic Name
estra-1,3,5(10)-triene-3,17α-diol
Synonyms
- 17alpha-Estradiol
LM ID
LMST02010029
Formula
Exact Mass
Calculate m/z
272.17763
Sum Composition
Status
Curated
3D model of Estradiol-17alpha
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
17α-Estradiol is the natural optical isomer of 17β-estradiol , the major estrogen secreted by the premenopausal ovary. 17α-Estradiol is a less active isomer than its counterpart, displaying 100-fold lower estrogenic activity relative to 17β-estradiol.1 It can inhibit 5α-reductase, which plays a role in regulating hair growth. 17α -estradiol is reported to activate the MAPK/ERK and PI3K-Akt signaling pathways via activation of the estrogen receptor-X and has been shown to be neuroprotective after an ischemic stroke and oxidative stress and in transgenic mice with Alzheimer’s disease.1,2
This information has been provided by Cayman Chemical
References
References
String Representations
InChiKey (Click to copy)
VOXZDWNPVJITMN-SFFUCWETSA-N
InChi (Click to copy)
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1
SMILES (Click to copy)
[C@@]12([H])CC[C@@H](O)[C@@]1(C)CC[C@]1([H])C3C=CC(O)=CC=3CC[C@@]21[H]
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
20
Rings
4
Aromatic Rings
1
Rotatable Bonds
0
Van der Waals Molecular Volume
269.28
Topological Polar Surface Area
40.46
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
2
logP
3.90
Molar Refractivity
79.24
Admin
Created at
-
Updated at
20th Feb 2025