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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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 |
HVYWMOMLDIMFJA-DPAQBDIFSA-N |
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 |
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Mus musculus
(NCBI:txid10090)
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See:
PubMed
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Daphnia galeata
(NCBI:txid27404)
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See:
PubMed
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Chlamydomonas reinhardtii
(NCBI:txid3055)
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See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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See:
DOI
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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.
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View more via ChEBI Ontology
Outgoing
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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)
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Incoming
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(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)
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(3β,14β,17α)-cholest-5-en-3-ol
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IUPAC
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Cholest-5-en-3beta-ol
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KEGG COMPOUND
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Cholesterin
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NIST Chemistry WebBook
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Cholesterol
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KEGG COMPOUND
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CHOLESTEROL
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PDBeChem
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cholesterol
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UniProt
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2060565
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Reaxys Registry Number
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Reaxys
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550297
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Gmelin Registry Number
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Gmelin
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57-88-5
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CAS Registry Number
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KEGG COMPOUND
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57-88-5
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CAS Registry Number
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ChemIDplus
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57-88-5
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CAS Registry Number
|
NIST Chemistry WebBook
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