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



Classification

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

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
17alpha-estradiol: a brain-active estrogen?,
Endocrinology, 2005
Pubmed ID: 15947006

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

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
GuidePharm ID

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

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Created at
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Updated at
20th Feb 2025