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Structure Database (LMSD)

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Common Name

7beta-hydroxycholesterol

Systematic Name

5-cholestene-3β,7β-diol

Synonyms

LM ID

LMST01010047

Formula

C₂₇H₄₆O₂

Exact Mass

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402.34978

Sum Composition

ST 27:1;O2

Status

Curated

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Classification

Biological Context

7β-hydroxy Cholesterol is an oxysterol formed by enzymatic and non-enzymatic oxidation of cholesterol.¹ It is the primary oxysterol found in LDL and induces apoptosis and cell death of human umbilical vein endothelial cells (HUVECs) in vitro in a concentration-dependent manner. Increased plasma levels of 7β-hydroxy cholesterol positively correlate with mortality in coronary heart disease in human males.²

This information has been provided by Cayman Chemical

References

1. Ziedén, B., Kaminskas, A., Kristenson, M., et al. Increased plasma 7 β-hydroxycholesterol concentrations in a population with a high risk for cardiovascular disease. Artioscler. Thromb. Vasc. Biol. 19(4), 967-971 (1999).

2. Lizard, G., Monier, S., Cordelet, C., et al. Characterization and comparison of the mode of cell death, apoptosis versus necrosis, induced by 7β-hydroxycholesterol and 7-ketocholesterol in the cells of the vascular wall. Arterioscler. Thromb. Vasc. Biol. 19(5), 1190-1200 (1999).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Equus caballus (#9796)

Mammalia (#40674)

THE ISOLATION OF 7(β)-HYDROXYCHOLESTEROL FROM THE SERUM OF PREGNANT MARES,
J Biol Chem, 1936

DOI: 10.1016/S0021-9258(18)73029-9

String Representations

InChiKey (Click to copy)

OYXZMSRRJOYLLO-KGZHIOMZSA-N

InChi (Click to copy)

InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24+,25+,26+,27-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCCC(C)C)CC[C@@]4([H])[C@]3([H])[C@@H](O)C=C2C[C@@H](O)C1