Structure Database (LMSD)

Common Name
16-Ketoestradiol
Systematic Name
3,17β-dihydroxy-estra-1,3,5(10)-trien-16-one
Synonyms
  • 16-oxoestradiol
LM ID
LMST02010047
Formula
C18H22O3
Exact Mass
Calculate m/z
286.156895
Sum Composition
ST 18:4;O3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroids [ST02]
C18 steroids (estrogens) and derivatives [ST0201]

Biological Context

16-Ketoestradiol is an active metabolite of the endogenous estrogen estrone .1 It is formed from estrone via an estriol or a 16-epiestriol intermediate by oxidation of the C-16 hydroxyl. 16-Ketoestradiol binds to estrogen receptor α (ERα) and ERβ with IC50 values of 112.2 and 50.1 nM for the human receptors, respectively.2 Intravaginal administration of 16-ketoestradiol increases vaginal epithelial thickness, stratification, and cornification in mice, indicating antiestrogenic activity.3

This information has been provided by Cayman Chemical

References

1. Brinton, L.A., Trabert, B., Anderson, G.L., et al. Serum estrogens and estrogen metabolites and endometrial cancer risk among postmenopausal women. Cancer Epidemiol. Biomarkers Prev. 25(7), 1081-1089 (2016).
2. Zhu, B.T., Han, G.-Z., Shim, J.-Y., et al. Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor α and β subtypes: Insights into the structural determinants favoring a differential subtype binding. Endocrinology 147(9), 4132-4150 (2006).
3. Martin, L. Dimethylstilbestrol and 16-oxo-estradiol: Anti-estrogens or estrogens? Steroids 13(1), 1-10 (1969).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
The conversion of estradiol-17beta-16-C14 to radioactive 16-ketoestradiol-17beta-in man.,
J Biol Chem, 1956
Pubmed ID: 13367066

String Representations

InChiKey (Click to copy)
KJDGFQJCHFJTRH-YONAWACDSA-N
InChi (Click to copy)
InChI=1S/C18H22O3/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/h3,5,8,13-15,17,19,21H,2,4,6-7,9H2,1H3/t13-,14-,15+,17+,18+/m1/s1
SMILES (Click to copy)
[C@@]12([H])CCC3C=C(O)C=CC=3[C@@]1([H])CC[C@]1(C)[C@@H](O)C(=O)C[C@@]21[H]

Other Databases

KEGG ID
C14383
HMDB ID
HMDB0000406
CHEBI ID
34165
PubChem CID
66417
Cayman ID
36033

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 4
Aromatic Rings 1
Rotatable Bonds 0
Van der Waals Molecular Volume 275.43
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 3.07
Molar Refractivity 79.63

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Created at
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Updated at
22nd Mar 2024