Structure Database (LMSD)
Common Name
4beta-hydroxy-cholesterol(d7)
Systematic Name
cholest-5-en-3β,4β-diol(d7)
Synonyms
3D model of 4beta-hydroxy-cholesterol(d7)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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]
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Created at
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Updated at
29th Jan 2021