cholesterol

Also known as cholest-5-en-3β-ol, Cholesterin, Hydrocerin, Cholest-5-en-3b-ol, Cordulan, Cholesterine, 5:6-Cholesten-3-ol, Dusoran

Cholesterol is the principal sterol of all animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.

OverviewAI-generated

Cholesterol is a chemical compound with the formula C₂₇H₄₆O. Its molecular mass is 386.35486609199995, while PubChem lists the weight as 386.7. The substance has a melting point of 149 and a boiling point of 200. It possesses a charge of 0 and contains one hydrogen bond donor and one hydrogen bond acceptor.

The compound is associated with the InChIKey HVYWMOMLDIMFJA-DPAQBDIFSA-N and an xlogP value of 8.7. Its topological polar surface area is 20.2. Cholesterol is the subject of 365,660 PubMed articles. Additionally, it is referenced by 2,832 other encyclopedia articles.

Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula: C27H46O
Molecular weight: 386.7 g/mol
IUPAC name: (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
InChIKey: HVYWMOMLDIMFJA-DPAQBDIFSA-N
XLogP: 8.7
Polar surface area: 20.2 Å²
H-bond donors: 1
H-bond acceptors: 1
Formal charge: 0

via PubChem

Research

365,660 papers

Cholesterol Review: A Metabolically Important Molecule.ReviewEndocrine practice : official journal of the American College of Endocrinology and the American Association of Clinical Endocrinologists · 2020Schade DS, Shey L, Eaton RPDOI: 10.4158/EP-2020-0347
The shared role of cholesterol in neuronal and peripheral inflammation.ReviewPharmacology & therapeutics · 2023Hansen SB, Wang HDOI: 10.1016/j.pharmthera.2023.108486
Cholesterol metabolism: molecular mechanisms, biological functions, diseases, and therapeutic targets.ReviewMolecular biomedicine · 2025Cui D, Yu X, Guan Q et al.DOI: 10.1186/s43556-025-00321-3
Cholesterol and Immune Microenvironment: Path Towards Tumorigenesis.ReviewCurrent nutrition reports · 2024Saad EE, Michel R, Borahay MADOI: 10.1007/s13668-024-00542-y
Cholesterol metabolism on stem cell fate determination: a frontier horizon.ReviewStem cell research & therapy · 2025Xu B, Li L, Wei Q et al.DOI: 10.1186/s13287-025-04687-7
Cationic cholesterol-dependent LNP delivery to lung stem cells, the liver, and heart.Proceedings of the National Academy of Sciences of the United States of America · 2024Radmand A, Kim H, Beyersdorf J et al.DOI: 10.1073/pnas.2307801120
[Cholesterol metabolism].ReviewKlinische Wochenschrift · 1970Weis HJDOI: 10.1007/BF01487127
Cholesterol metabolism in pancreatic cancer and associated therapeutic strategies.ReviewBiochimica et biophysica acta. Molecular and cell biology of lipids · 2025Daya T, Breytenbach A, Gu L et al.DOI: 10.1016/j.bbalip.2024.159578

via PubMed

~36 min read

Encyclopedic overview

27 sections

Contents

Etymology
Physiology
Function
Membranes
Substrate presentation
Signaling
As a chemical precursor
Epidermis
Metabolism
Biosynthesis and regulation
Biosynthesis
Regulation of cholesterol synthesis
Plasma transport and regulation of absorption
Metabolism, recycling and excretion
Dietary sources
Medical guidelines and recommendations
Clinical significance
Hypercholesterolemia
Hypocholesterolemia
Testing
Interactive pathway map
Cholesteric liquid crystals
Stereoisomers
Additional images
See also
References
External links

Cholesterol is the principal sterol of all animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.

Cholesterol is biosynthesized by all animal cells and is an essential structural and signaling component of animal cell membranes. In vertebrates, hepatic cells typically produce the greatest amounts. In the brain, astrocytes produce cholesterol and transport it to neurons. It is absent among prokaryotes (bacteria and archaea), although there are some exceptions, such as Mycoplasma, which require cholesterol for growth. Cholesterol also serves as a precursor for the biosynthesis of steroid hormones, bile acid, and vitamin D.

Excerpted from Wikipedia’s “cholesterol” article, available under the CC BY-SA 4.0 licence.