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CHEBI:16113 - cholesterol

Default Structure
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
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
Daphnia galeata (ncbitaxon:27404) - PubMed (12816661)
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Mus musculus (ncbitaxon:10090)
- PubMed (4696527)
- PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Biological Roles:
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Daphnia galeata metabolite  A Daphnia metabolite produced by the species Daphnia galeata.
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).
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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 antineoplastic agent (CHEBI:35610)
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
(3β,14β,17α)-cholest-5-en-3-olIUPAC
Cholest-5-en-3beta-olKEGG COMPOUND
Cholest-5-en-3-ol (3.beta.)-ChEMBL
CholesterinNIST Chemistry WebBook
CholesterinumChEMBL
CholesterolKEGG COMPOUND
Brand Names  Source
Cholesterol component of alfChEMBL
Cholesterol component of alf43ChEMBL
Cholesterol component of alfqChEMBL
Cholesterol component of army liposome formulationChEMBL
UniProt Name  Source
cholesterolUniProt
Manual XrefsDatabases
C00003648KNApSAcK
C00187KEGG COMPOUND
CholesterolWikipedia
CHOLESTEROLMetaCyc
CLRPDBeChem
D00040KEGG DRUG
DB04540DrugBank
HMDB0000067HMDB
LMST01010001LIPID MAPS
Registry NumbersSources
Reaxys:2060565Reaxys
Gmelin:550297Gmelin
CAS:57-88-5NIST Chemistry WebBook
CAS:57-88-5KEGG COMPOUND
CAS:57-88-5ChemIDplus
Citations