LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG SVG

Common Name

4beta-hydroxy-cholesterol(d7)

Systematic Name

cholest-5-en-3β,4β-diol(d7)

Synonyms

LM ID

LMST01010003

Formula

C₂₇H₃₉D₇O₂

Exact Mass

Calculate m/z

409.393718

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

4β-hydroxy Cholesterol-d7 is intended for use as an internal standard for the quantification of 4β-hydroxy cholesterol by GC- or LC-MS. 4β-hydroxy Cholesterol is a major oxysterol cholesterol metabolite and a precursor in the synthesis of bile acids that is found in human circulation.¹ It is formed from cholesterol by the cytochrome P450 (CYP) isoforms CYP3A4 and CYP3A5.1 4β-hydroxy Cholesterol has an unusually long half-life in plasma (~60 hours) as a result of slow elimination, particularly due to a slow rate of 7α-hydroxylation, which is the rate-limiting step for further conversion into bile acids.

This information has been provided by Cayman Chemical

References

1. Dicfalusy, U., Kanebratt, K.P., Bredberg, E., et al. 4β-Hydroxycholesterol as an endogenous marker for CYP3A4/5 activity. Stability and half-life of elimination after induction with rifampicin. Br. J. Clin. Pharmacol. 67(1), 38-43 (2009).

References

Comments

Synthetic deuterated standard

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

CZDKQKOAHAICSF-BZNWTYAPSA-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/i1D3,2D3,17D

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([2H])([2H])[2H])(C([2H])([2H])[2H])[2H])CC[C@@]21[H])[H]