LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

4-hydroxyestradiol

Systematic Name

estra-1,3,5(10)-triene-2,4,17β-triol

Synonyms

LM ID

LMST02010028

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

Classification

Biological Context

4-Hydroxyestradiol is a catechol estrogen and minor metabolite of estrogen.^1,2 4-Hydroxyestradiol is formed from estrogen by the cytochrome P450 (CYP) isoform CYP1B1.2 Production of 4-hydroxyestradiol is increased in microsomes prepared from human mammary adenocarcinoma and fibroadenoma microsomes compared with microsomes prepared from non-cancerous tissues.¹ 4-Hydroxyestradiol (25 mg/animal) induces renal tumor formation in male hamsters.³

This information has been provided by Cayman Chemical

References

1. Liehr, J.C., and Ricci, M.J. 4-Hydroxylation of estrogens as marker of human mammary tumors. Proc. Natl. Acad. Sci. USA 93(8), 3294-3296 (1996).

2. Yager, J.D., and Liehr, J.G. Molecular mechanisms of estrogen carcinogenesis. Annu. Rev. Pharmacol. Toxicol. 36, 203-232 (1996).

3. Liehr, J.G., Fang, W.F., Sirbasku, D.A., et al. Carcinogenicity of catechol estrogens in Syrian hamsters. J. Steroid Biochem. 24(1), 353-356 (1986).

Reactions

Filter by species:

Click on an edge to display the reaction(s).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

4-Hydroxylation of estrogens as marker of human mammary tumors.,
Proc Natl Acad Sci U S A, 1996

Pubmed ID: 8622931

String Representations

InChiKey (Click to copy)

QOZFCKXEVSGWGS-ZHIYBZGJSA-N

InChi (Click to copy)

InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1

SMILES (Click to copy)

C1=CC2[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])CCC=2C(O)=C1O