LIPID MAPS

Structure Database (LMSD)

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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

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

DOI: 10.1042/bj0590136

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