CHEBI:16113 - cholesterol

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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:CB9382699, ChemicalBook:CB6382698, eMolecules:524891
Download Molfile XML SDF
Wikipedia License
Retinal (also known as retinaldehyde) is a polyene chromophore. Retinal, bound to proteins called opsins, is the chemical basis of visual phototransduction, the light-detection stage of visual perception (vision). Some microorganisms use retinal to convert light into metabolic energy. One study suggests that approximately three billion years ago, most living organisms on Earth used retinal, rather than chlorophyll, to convert sunlight into energy. Because retinal absorbs mostly green light and transmits purple light, this gave rise to the Purple Earth hypothesis. Retinal itself is considered to be a form of vitamin A when eaten by an animal. There are many forms of vitamin A, all of which are converted to retinal, which cannot be made without them. The number of different molecules that can be converted to retinal varies from species to species. Retinal was originally called retinene, and was renamed after it was discovered to be vitamin A aldehyde. Vertebrate animals ingest retinal directly from meat, or they produce retinal from carotenoids – either from α-carotene or β-carotene – both of which are carotenes. They also produce it from β-cryptoxanthin, a type of xanthophyll. These carotenoids must be obtained from plants or other photosynthetic organisms. No other carotenoids can be converted by animals to retinal. Some carnivores cannot convert any carotenoids at all. The other main forms of vitamin A – retinol and a partially active form, retinoic acid – may both be produced from retinal. Invertebrates such as insects and squid use hydroxylated forms of retinal in their visual systems, which derive from conversion from other xanthophylls.
Read full article at Wikipedia
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 Types Sources
10901445 PubMed citation Europe PMC
11412894 PubMed citation Europe PMC
16341241 PubMed citation Europe PMC
24287311 PubMed citation Europe PMC
25308664 PubMed citation Europe PMC
25451949 PubMed citation Europe PMC
25522988 PubMed citation Europe PMC
25658343 PubMed citation Europe PMC
25977713 PubMed citation Europe PMC
4696527 PubMed citation Europe PMC
8838010 PubMed citation Europe PMC
Last Modified
11 February 2022