Structure Database (LMSD)

Common Name
16-Epiestriol
Systematic Name
estra-1,3.5(10)-triene-3,16β,17β-triol
Synonyms
  • 16-epioestriol
LM ID
LMST02010006
Formula
C18H24O3
Exact Mass
Calculate m/z
288.172545
Sum Composition
ST 18:3;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-Epiestriol is a metabolite of the endogenous estrogen estrone .1 It is formed from estrone via a 16β-hydroxy estrone intermediate by reduction of the C-17 ketone. 16-Epiestriol (200 µg/ml) inhibits the growth of carbapenem-resistant A. baumannii.2 It inhibits carrageenan-induced paw edema in rats when administered at a dose of 20 mg/kg.3 Unlike hydrocortisone, 16-epiestriol (240 µg/animal) does not increase plasma or liver glucose levels in adrenalectomized rats.

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. Skariyachan, S., Muddebihalkar, A.G., Badrinath, V., et al. Natural epiestriol-16 act as potential lead molecule against prospective molecular targets of multidrug resistant Acinetobacter baumannii-Insight from in silico modelling and in vitro investigations. Infect. Genet. Evol. 82, 104314 (2020).
3. Latman, N.S., Kishore, V., and Bruot, B.C. 16-Epiestriol: An anti-inflammatory steroid without glycogenic activity. J. Pharm. Sci. 83(6), 874-877 (1994).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
The isolation of 16-epioestriol from the urine of pregnant women.,
Biochem J, 1955
Pubmed ID: 14351154

String Representations

InChiKey (Click to copy)
PROQIPRRNZUXQM-ZMSHIADSSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1C2[C@@]3([H])CC[C@]4(C)[C@@H](O)[C@@H](O)C[C@@]4([H])[C@]3([H])CCC=2C=C(O)C=1

Other Databases

HMDB ID
HMDB0000347
CHEBI ID
87620
LIPIDBANK ID
SST0062
PubChem CID
68929
SwissLipids ID
SLM:000501377
Cayman ID
33455

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 4
Aromatic Rings 1
Rotatable Bonds 0
Van der Waals Molecular Volume 278.07
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 3.15
Molar Refractivity 81.14

Admin

Created at
-
Updated at
4th Jan 2024