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

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (S)-2,3-epoxysqualene
ChEBI ID CHEBI:15441
ChEBI ASCII Name (S)-2,3-epoxysqualene
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:18728, CHEBI:11026, CHEBI:11072, CHEBI:372
Supplier Information ChemicalBook:CB6164395, ChemicalBook:CB9164396, ChemicalBook:CB1940606, eMolecules:494417, ZINC000000039811
Download Molfile XML SDF
Formula C30H50O
Net Charge 0
Average Mass 426.71740
Monoisotopic Mass 426.38617
InChI InChI=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
InChIKey QYIMSPSDBYKPPY-RSKUXYSASA-N
SMILES CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Homo sapiens (NCBI:txid9606) 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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (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 Sources
(3S)-2,3-dihydro-2,3-epoxysqualene ChEBI
(3S)-2,3-epoxy-2,3-dihydrosqualene ChEBI
(S)-2,3-dihydro-2,3-epoxysqualene ChEBI
(S)-2,3-epoxy-2,3-dihydrosqualene ChEBI
(S)-2,3-Epoxysqualene KEGG COMPOUND
(S)-2,3-epoxysqualene ChEBI
(S)-2,3-epoxysqualene UniProt
(S)-2,3-oxidosqualene ChEBI
(S)-Squalene-2,3-epoxide KEGG COMPOUND
(S)-squalene-2,3-epoxide ChEBI
2,3-EDSQ MetaCyc
2,3-epoxisqualene MetaCyc
2,3-oxidosqualene MetaCyc
oxidosqualene MetaCyc
Squalene 2,3-epoxide KEGG COMPOUND
Squalene 2,3-oxide KEGG COMPOUND
Manual Xrefs Databases
2TX PDBeChem
C00007282 KNApSAcK
C01054 KEGG COMPOUND
EPOXYSQUALENE MetaCyc
HMDB0001188 HMDB
HMDB0059621 HMDB
LMPR0106010010 LIPID MAPS
View more database links
Registry Number Type Source
4710524 Reaxys Registry Number Reaxys
Citations Types Sources
19951700 PubMed citation Europe PMC
26058429 PubMed citation Europe PMC
Last Modified
28 April 2020