Structure Database (LMSD)

Common Name
Cholesterol(d7)
Systematic Name
cholest-5-en-3β-ol(d7)
Synonyms
LM ID
LMST01010093
Formula
Exact Mass
Calculate m/z
393.398804
Status
Curated

Classification

Biological Context

Cholesterol-d7 is intended for use as an internal standard for the quantification of cholesterol by GC- or LC-MS. Cholesterol is a major sterol produced in mammalian cells that is required for cell viability and proliferation.1 It is a component of mammalian cell membranes that interacts with membrane phospholipids, sphingolipids, and proteins to influence their behavior. It is also a component of various lipid-based drug delivery (LBDD) systems, including liposomes and lipid nanoparticles (LNPs), where it has a role in membrane stability.2 Cholesterol is a precursor of steroid hormones, bile acids, and the active form of vitamin D. Impaired cholesterol homeostasis is related to the development of various diseases including fatty liver, diabetes, gallstones, dyslipidemia, atherosclerosis, heart attack, and stroke.3

This information has been provided by Cayman Chemical

References

1. Ohvo-Rekilä, H., Ramstedt, B., Leppimäki, P., et al. Cholesterol interactions with phospholipids in membranes. Prog. Lipid Res. 41(1), 66-97 (2002).
2. Yamanashi, Y., Takada, T., and Suzuki, H. Associations between lifestyle-related diseases and transporters involved in intestinal absorption and biliary excretion of cholesterol. Biol. Pharm. Bull. 41(1), 1-10 (2018).

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)
HVYWMOMLDIMFJA-IFAPJKRJSA-N
InChi (Click to copy)
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1/i1D3,2D3,18D
SMILES (Click to copy)
[C@]12(CC=C3C[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]

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
Avanti ID

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Created at
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Updated at
9th Jun 2022