LIPID MAPS

Structure Database (LMSD)

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Common Name

Cholesterol

Systematic Name

cholest-5-en-3β-ol

Synonyms

Cholesterol
Cholest-5-en-3-ol
(3beta)-Cholest-5-en-3-ol
Cholesteryl alcohol

LM ID

LMST01010001

Formula

C₂₇H₄₆O

Exact Mass

Calculate m/z

386.354865

Sum Composition

ST 27:1;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

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 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).

3. Tenchov, R., Bird, R., Curtze, A.E., et al. Lipid nanoparticles-from liposomes to mRNA vaccine delivery, a landscape of research diversity and advancement. ACS Nano 15(11), 16982-17015 (2021).

Reactions

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

Mus musculus (#10090)

Mammalia (#40674)

Subcellular organelle lipidomics in TLR-4-activated macrophages.,
J Lipid Res, 2010

Pubmed ID: 20574076

DOI: 10.1194/jlr.M008748

String Representations

InChiKey (Click to copy)

HVYWMOMLDIMFJA-DPAQBDIFSA-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

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