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CHEBI:16113 - cholesterol

ChEBI IDCHEBI:16113
ChEBI Namecholesterol
Stars
DefinitionA cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3β-hydroxy group.
Secondary ChEBI IDsCHEBI:3659, CHEBI:13982, CHEBI:23204, CHEBI:41564
Last Modified11 February 2022
DownloadsMolfile
FormulaC27H46O
Net Charge0
Average Mass386.664
Monoisotopic Mass386.35487
SMILES[H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@]1([H])[C@H](C)CCCC(C)C
InChIInChI=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
InChIKeyHVYWMOMLDIMFJA-DPAQBDIFSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Daphnia galeata (ncbitaxon:27404) - PubMed (12816661)
Mus musculus (ncbitaxon:10090)
- PubMed (4696527)
- PubMed (19425150) Source: BioModels - MODEL1507180067
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
Roles Classification
Biological Roles:
Daphnia galeata metabolite  A Daphnia metabolite produced by the species Daphnia galeata.
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
(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-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)-3β,26-dihydroxycholest-5-en-7-one (CHEBI:87653) 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)
7-aminocholesterol (CHEBI:77845) has functional parent cholesterol (CHEBI:16113)
7-ketocholesterol (CHEBI:64294) has functional parent cholesterol (CHEBI:16113)
7α-hydroxycholesterol (CHEBI:17500) 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)
7β-hydroxycholesterol (CHEBI:42989) has functional parent cholesterol (CHEBI:16113)
cholesterol sulfate (CHEBI:41321) has functional parent cholesterol (CHEBI:16113)
cholesteryl butyrate (CHEBI:746898) 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)
cholesteryl β-D-glucoside (CHEBI:17495) 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  Source
CholesterolKEGG COMPOUND
Cholest-5-en-3beta-olKEGG COMPOUND
CHOLESTEROLPDBeChem
CholesterinNIST Chemistry WebBook
(3β,14β,17α)-cholest-5-en-3-olIUPAC
UniProt Name  Source
cholesterolUniProt
Manual XrefsDatabases
C00187KEGG COMPOUND
LMST01010001LIPID MAPS
CLRPDBeChem
DB04540DrugBank
CholesterolWikipedia
CHOLESTEROLMetaCyc
HMDB0000067HMDB
C00003648KNApSAcK
D00040KEGG DRUG
Registry NumbersSources
Gmelin:550297Gmelin
Reaxys:2060565Reaxys
CAS:57-88-5KEGG COMPOUND
CAS:57-88-5ChemIDplus
CAS:57-88-5NIST Chemistry WebBook
Citations