CHEBI:16113 - cholesterol

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ChEBI Name cholesterol
ChEBI ID CHEBI:16113
Definition A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3β-hydroxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41564, CHEBI:3659, CHEBI:13982, CHEBI:23204
Supplier Information ChemicalBook:CB3167375, ChemicalBook:CB4183426, eMolecules:494487, ZINC000000899824
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Cholesterol is the principal sterol of all higher 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. Elevated levels of cholesterol in the blood, especially when bound to low-density lipoprotein (LDL, often referred to as "bad cholesterol"), may increase the risk of cardiovascular disease. François Poulletier de la Salle first identified cholesterol in solid form in gallstones in 1769. In 1815, chemist Michel Eugène Chevreul named the compound "cholesterine".
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Formula C27H46O
Net Charge 0
Average Mass 386.655
Monoisotopic Mass 386.35487
InChI 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
InChIKey HVYWMOMLDIMFJA-DPAQBDIFSA-N
SMILES C1[C@@]2([C@]3(CC[C@]4([C@]([C@@]3(CC=C2C[C@H](C1)O)[H])(CC[C@@]4([C@H](C)CCCC(C)C)[H])[H])C)[H])C
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: PubMed
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Daphnia galeata (NCBI:txid27404) See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Daphnia galeata metabolite
A Daphnia metabolite produced by the species Daphnia galeata.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cholesterol (CHEBI:16113) has role Daphnia galeata metabolite (CHEBI:83038)
cholesterol (CHEBI:16113) has role algal metabolite (CHEBI:84735)
cholesterol (CHEBI:16113) has role human metabolite (CHEBI:77746)
cholesterol (CHEBI:16113) has role mouse metabolite (CHEBI:75771)
cholesterol (CHEBI:16113) is a 3β-hydroxy-Δ5-steroid (CHEBI:1722)
cholesterol (CHEBI:16113) is a 3β-sterol (CHEBI:35348)
cholesterol (CHEBI:16113) is a C27-steroid (CHEBI:131619)
cholesterol (CHEBI:16113) is a cholestanoid (CHEBI:50401)
Incoming (16S,22S)-dihydroxycholesterol (CHEBI:191938) has functional parent cholesterol (CHEBI:16113)
(20R)-17α,20-dihydroxycholesterol (CHEBI:783) has functional parent cholesterol (CHEBI:16113)
(20S)-17α,20-dihydroxycholesterol (CHEBI:182953) has functional parent cholesterol (CHEBI:16113)
(22R)-22-hydroxycholesterol (CHEBI:67237) has functional parent cholesterol (CHEBI:16113)
(22S)-22-hydroxycholesterol (CHEBI:1301) has functional parent cholesterol (CHEBI:16113)
(24S,25)-dihydroxycholesterol (CHEBI:86074) has functional parent cholesterol (CHEBI:16113)
(24S,26)-dihydroxycholesterol (CHEBI:86075) has functional parent cholesterol (CHEBI:16113)
(25R)-3β,26-dihydroxycholest-5-en-7-one (CHEBI:87653) has functional parent cholesterol (CHEBI:16113)
(25R)-3β-hydroxycholest-5-en-7-one-26-al (CHEBI:87677) has functional parent cholesterol (CHEBI:16113)
(25R)-3β-hydroxycholest-5-en-7-one-26-oic acid (CHEBI:87783) has functional parent cholesterol (CHEBI:16113)
(25R)-cholest-5-ene-3β,26-diol (CHEBI:76591) has functional parent cholesterol (CHEBI:16113)
24-hydroxycholesterol (CHEBI:50515) has functional parent cholesterol (CHEBI:16113)
24-methylenecholesterol (CHEBI:19812) has functional parent cholesterol (CHEBI:16113)
25-hydroxycholesterol (CHEBI:42977) has functional parent cholesterol (CHEBI:16113)
26-hydroxycholesterol (CHEBI:17703) has functional parent cholesterol (CHEBI:16113)
3β-hydroxycholest-5-en-26-al (CHEBI:84145) has functional parent cholesterol (CHEBI:16113)
3β-hydroxycholest-5-en-26-oic acid (CHEBI:81014) has functional parent cholesterol (CHEBI:16113)
4β-hydroxycholesterol (CHEBI:85778) has functional parent cholesterol (CHEBI:16113)
7α,24-dihydroxycholesterol (CHEBI:50517) has functional parent cholesterol (CHEBI:16113)
7α,25-dihydroxycholesterol (CHEBI:37623) has functional parent cholesterol (CHEBI:16113)
7α,26-dihydroxycholesterol (CHEBI:18431) has functional parent cholesterol (CHEBI:16113)
7α-hydroxycholesterol (CHEBI:17500) has functional parent cholesterol (CHEBI:16113)
7β-hydroxycholesterol (CHEBI:42989) has functional parent cholesterol (CHEBI:16113)
7-aminocholesterol (CHEBI:77845) has functional parent cholesterol (CHEBI:16113)
7-ketocholesterol (CHEBI:64294) has functional parent cholesterol (CHEBI:16113)
cholesterol sulfate (CHEBI:41321) has functional parent cholesterol (CHEBI:16113)
cholesteryl β-D-glucoside (CHEBI:17495) has functional parent cholesterol (CHEBI:16113)
cholesteryl ester (CHEBI:17002) has functional parent cholesterol (CHEBI:16113)
cholesteryl glycoside (CHEBI:61656) has functional parent cholesterol (CHEBI:16113)
cholesteryl hemisuccinate (CHEBI:138742) has functional parent cholesterol (CHEBI:16113)
Glycino 3β-cholesterol ester group (CHEBI:143135) has functional parent cholesterol (CHEBI:16113)
oxysterol (CHEBI:53030) has functional parent cholesterol (CHEBI:16113)
cholesteryl β-D-galactoside (CHEBI:189066) has part cholesterol (CHEBI:16113)
cholesteryl β-D-xyloside (CHEBI:189067) has part cholesterol (CHEBI:16113)
IUPAC Name
cholest-5-en-3β-ol
Synonyms Sources
(3β,14β,17α)-cholest-5-en-3-ol IUPAC
Cholest-5-en-3beta-ol KEGG COMPOUND
Cholesterin NIST Chemistry WebBook
Cholesterol KEGG COMPOUND
CHOLESTEROL PDBeChem
cholesterol UniProt
Manual Xrefs Databases
C00003648 KNApSAcK
C00187 KEGG COMPOUND
Cholesterol Wikipedia
CHOLESTEROL MetaCyc
CLR PDBeChem
D00040 KEGG DRUG
DB04540 DrugBank
HMDB0000067 HMDB
LMST01010001 LIPID MAPS
View more database links
Registry Numbers Types Sources
2060565 Reaxys Registry Number Reaxys
550297 Gmelin Registry Number Gmelin
57-88-5 CAS Registry Number KEGG COMPOUND
57-88-5 CAS Registry Number ChemIDplus
57-88-5 CAS Registry Number NIST Chemistry WebBook
Citations
Morzycki JW, Sobkowiak A (2015)
Electrochemical oxidation of cholesterol.
Beilstein journal of organic chemistry 11, 392-402 [PubMed:25977713]
[show Abstract]
Levinson SS, Wagner SG (2015)
Implications of reverse cholesterol transport: recent studies.
Clinica chimica acta; international journal of clinical chemistry 439, 154-161 [PubMed:25451949]
[show Abstract]
Iaea DB, Maxfield FR (2015)
Cholesterol trafficking and distribution.
Essays in biochemistry 57, 43-55 [PubMed:25658343]
[show Abstract]
Derewiaka D, Molińska née Sosińska E (2015)
Cholesterol transformations during heat treatment.
Food chemistry 171, 233-240 [PubMed:25308664]
[show Abstract]
Favari E, Chroni A, Tietge UJ, Zanotti I, Escolà-Gil JC, Bernini F (2015)
Cholesterol efflux and reverse cholesterol transport.
Handbook of experimental pharmacology 224, 181-206 [PubMed:25522988]
[show Abstract]
Varbo A, Benn M, Nordestgaard BG (2014)
Remnant cholesterol as a cause of ischemic heart disease: evidence, definition, measurement, atherogenicity, high risk patients, and present and future treatment.
Pharmacology & therapeutics 141, 358-367 [PubMed:24287311]
[show Abstract]
Kanter JL, Narayana S, Ho PP, Catz I, Warren KG, Sobel RA, Steinman L, Robinson WH (2006)
Lipid microarrays identify key mediators of autoimmune brain inflammation.
Nature medicine 12, 138-143 [PubMed:16341241]
[show Abstract]
Haines TH (2001)
Do sterols reduce proton and sodium leaks through lipid bilayers?
Progress in lipid research 40, 299-324 [PubMed:11412894]
[show Abstract]
Motamed Khorasani A, Cheung AP, Lee CY (2000)
Cholesterol inhibitory effects on human sperm-induced acrosome reaction.
Journal of andrology 21, 586-594 [PubMed:10901445]
[show Abstract]
Cross NL (1996)
Human seminal plasma prevents sperm from becoming acrosomally responsive to the agonist, progesterone: cholesterol is the major inhibitor.
Biology of reproduction 54, 138-145 [PubMed:8838010]
[show Abstract]
Weibust RS (1973)
Inheritance of plasma cholesterol levels in mice.
Genetics 73, 303-312 [PubMed:4696527]
[show Abstract]
Last Modified
11 February 2022