EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:15441 - (S)-2,3-epoxysqualene

ChEBI IDCHEBI:15441
ChEBI Name(S)-2,3-epoxysqualene
Stars
ASCII Name(S)-2,3-epoxysqualene
DefinitionA 2,3-epoxysqualene in which the chiral centre has S configuration. It is converted into lanosterol by lanosterol synthase (EC 5.4.99.7) in a key rate-limiting step in the biosynthesis of chloesterol, steroid hormones, and vitamin D.
Secondary ChEBI IDsCHEBI:372, CHEBI:11026, CHEBI:11072, CHEBI:18728
Last Modified28 April 2020
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC30H50O
Net Charge0
Average Mass426.729
Monoisotopic Mass426.38617
SMILESCC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C=C(\C)CC/C=C(\C)CC[C@@H]1OC1(C)C
InChIInChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+/t29-/m0/s1
InChIKeyQYIMSPSDBYKPPY-RSKUXYSASA-N
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Saccharomyces cerevisiae (ncbitaxon:4932) - PubMed (24678285) Source: yeast.sf.net
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Biological Roles:
Saccharomyces cerevisiae metabolite  Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
ChEBI Ontology
Outgoing Relation(s)
(S)-2,3-epoxysqualene (CHEBI:15441) has parent hydride squalene (CHEBI:15440)
(S)-2,3-epoxysqualene (CHEBI:15441) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
(S)-2,3-epoxysqualene (CHEBI:15441) has role human metabolite (CHEBI:77746)
(S)-2,3-epoxysqualene (CHEBI:15441) has role mouse metabolite (CHEBI:75771)
(S)-2,3-epoxysqualene (CHEBI:15441) is a 2,3-epoxysqualene (CHEBI:78662)
IUPAC Name 
(3S)-2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane
Synonyms  Source
(S)-2,3-EpoxysqualeneKEGG COMPOUND
Squalene 2,3-epoxideKEGG COMPOUND
Squalene 2,3-oxideKEGG COMPOUND
(S)-Squalene-2,3-epoxideKEGG COMPOUND
(S)-2,3-epoxysqualeneChEBI
(S)-squalene-2,3-epoxideChEBI
UniProt Name  Source
(S)-2,3-epoxysqualeneUniProt
Manual XrefsDatabases
C01054KEGG COMPOUND
C01054KEGG COMPOUND
C00007282KNApSAcK
2TXPDBeChem
LMPR0106010010LIPID MAPS
HMDB0001188HMDB
HMDB0059621HMDB
EPOXYSQUALENEMetaCyc
Registry NumbersSources
Reaxys:4710524Reaxys
Citations