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squalene (CHEBI:15440)

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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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Formulae Sources
C30H50 KEGG COMPOUND
C30H50 ChEBI
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 Sources
Isolated from Rubia yunnanensis (IPNI:765385-1) found in root (BTO:0001188) PubMed
Isolated from Homo sapiens (NCBI:9606) DOI
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing squalene (CHEBI:15440) has role human metabolite (CHEBI:77746)
squalene (CHEBI:15440) has role metabolite (CHEBI:25212)
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)
(S)-2,3-epoxysqualene (CHEBI:15441) has parent hydride squalene (CHEBI:15440)
2,3-epoxysqualene (CHEBI:78662) 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 NIST Chemistry WebBook
111-02-4 CAS Registry Number ChemIDplus
1728920 Beilstein Registry Number Beilstein
Citation Waiting for Citations Type Source
16341241 PubMed citation CiteXplore
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).
 
Last Modified
28 July 2014

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