CHEBI:15440 - squalene

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ChEBI Name squalene
ChEBI ID CHEBI:15440
Definition A triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:10843, CHEBI:9245, CHEBI:10795, CHEBI:15104, CHEBI:26746
Supplier Information
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Formula C30H50
Net Charge 0
Average Mass 410.71800
InChI InChI=1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+
InChIKey YYGNTYWPHWGJRM-AAJYLUCBSA-N
SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
Metabolite of Species Details
Rubia yunnanensis (IPNI:765385-1) Found in root (BTO:0001188). Methanolic extract of air dried powdered roots. See: PubMed
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Centella asiatica (NCBI:48106) See: MetaboLights Study
Saccharomyces cerevisiae (NCBI:4932) Source: yeast.sf.net See: PubMed
Homo sapiens (NCBI:9606) See: DOI
Roles Classification
Biological Role(s): Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing squalene (CHEBI:15440) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
squalene (CHEBI:15440) has role human metabolite (CHEBI:77746)
squalene (CHEBI:15440) has role mouse metabolite (CHEBI:75771)
squalene (CHEBI:15440) has role plant metabolite (CHEBI:76924)
squalene (CHEBI:15440) is a triterpene (CHEBI:35191)
Incoming 3,22-dimethyl-1,2,23,24-tetradehydro-2,3,22,23-tetrahydrosqualene (CHEBI:70861) has functional parent squalene (CHEBI:15440)
3-methyl-1,2-didehydro-2,3-dihydrosqualene (CHEBI:70860) has functional parent squalene (CHEBI:15440)
(R)-12-hydroxysqualene (CHEBI:88123) has parent hydride squalene (CHEBI:15440)
(S)-2,3-epoxysqualene (CHEBI:15441) has parent hydride squalene (CHEBI:15440)
2,3-epoxysqualene (CHEBI:78662) has parent hydride squalene (CHEBI:15440)
squalene triterpenoid (CHEBI:26747) has parent hydride squalene (CHEBI:15440)
tetrahydroxysqualene (CHEBI:66216) has parent hydride squalene (CHEBI:15440)
IUPAC Name
(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
Synonyms Sources
(all-E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene NIST Chemistry WebBook
Spinacene KEGG COMPOUND
Squalene KEGG COMPOUND
squalene UniProt
Supraene KEGG COMPOUND
Database Links Databases
C00003755 KNApSAcK
C00751 KEGG COMPOUND
LMPR0106010002 LIPID MAPS
View more database links
Registry Numbers Types Sources
111-02-4 CAS Registry Number KEGG COMPOUND
111-02-4 CAS Registry Number ChemIDplus
111-02-4 CAS Registry Number NIST Chemistry WebBook
1728920 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
16341241 PubMed citation CiteXplore
24362891 PubMed citation CiteXplore
Last Modified
27 January 2016
General Comment
2011-04-06 Squalene is the biochemical precursor to the whole family of steroids. Oxidation (via squalene monooxygenase) of one of the terminal double bonds of squalene yields 2,3-squalene oxide, which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids (Wikipedia).