LIPID MAPS

Structure Database (LMSD)

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Common Name

4alpha-hydroxy-cholesterol

Systematic Name

cholest-5-en-3β,4α-diol

Synonyms

LM ID

LMST01010509

Formula

C₂₇H₄₆O₂

Exact Mass

Calculate m/z

402.34978

Sum Composition

ST 27:1;O2

Status

Active

Show lipids differing only in stereochemistry/bond geometry

Main

Classification

String Representations

InChiKey (Click to copy)

CZDKQKOAHAICSF-GFYXKKFXSA-N

InChi (Click to copy)

InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25+,26-,27-/m1/s1

SMILES (Click to copy)

[C@]12(CC=C3[C@H](O)[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(C)C)CC[C@@]21[H])[H]

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

The oxysterols cholest-5-ene-3 beta,4 alpha-diol, cholest-5-ene-3 beta,4 beta-diol and cholestane-3 beta,5 alpha,6 alpha-triol are formed during in vitro oxidation of low density lipoprotein, and are present in human atherosclerotic plaques.,
Biochim Biophys Acta, 1996

Pubmed ID: 8695664