CHEBI:138307 - (3S,22S)-2,3:22,23-diepoxy-2,3,22,23-tetrahydrosqualene

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ChEBI Name (3S,22S)-2,3:22,23-diepoxy-2,3,22,23-tetrahydrosqualene
ChEBI ID CHEBI:138307
ChEBI ASCII Name (3S,22S)-2,3:22,23-diepoxy-2,3,22,23-tetrahydrosqualene
Definition A squalene triterpenoid obtained by epoxidation accross the 2,3- and 22,23-double bonds of squalene.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information ZINC000013509871
Download Molfile XML SDF
Formula C30H50O2
Net Charge 0
Average Mass 442.718
Monoisotopic Mass 442.38108
InChI InChI=1S/C30H50O2/c1-23(15-11-17-25(3)19-21-27-29(5,6)31-27)13-9-10-14-24(2)16-12-18-26(4)20-22-28-30(7,8)32-28/h13-14,17-18,27-28H,9-12,15-16,19-22H2,1-8H3/b23-13+,24-14+,25-17+,26-18+/t27-,28-/m0/s1
InChIKey KABSNIWLJXCBGG-OQSIWNGOSA-N
SMILES C(C/C=C(/CC/C=C(/CC[C@H]1C(O1)(C)C)\C)\C)/C=C(/CC/C=C(/CC[C@H]2C(O2)(C)C)\C)\C
Metabolite of Species Details
Lycopodium clavatum (NCBI:txid3252) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (3S,22S)-2,3:22,23-diepoxy-2,3,22,23-tetrahydrosqualene (CHEBI:138307) has role plant metabolite (CHEBI:76924)
(3S,22S)-2,3:22,23-diepoxy-2,3,22,23-tetrahydrosqualene (CHEBI:138307) is a epoxide (CHEBI:32955)
(3S,22S)-2,3:22,23-diepoxy-2,3,22,23-tetrahydrosqualene (CHEBI:138307) is a squalene triterpenoid (CHEBI:26747)
IUPAC Name
(2S,2'S)-2,2'-[(3E,7E,11E,15E)-3,7,12,16-tetramethyloctadeca-3,7,11,15-tetraene-1,18-diyl]bis(3,3-dimethyloxirane)
Synonyms Sources
(3S,22S)-2,3:22,23-diepoxysqualene UniProt
(3S,22S)-2,3:22,23-dioxidosqualene ChEBI
Manual Xref Database
CPD-20473 MetaCyc
View more database links
Registry Number Type Source
8657029 Reaxys Registry Number Reaxys
Citations
Araki T, Saga Y, Marugami M, Otaka J, Araya H, Saito K, Yamazaki M, Suzuki H, Kushiro T (2016)
Onocerin Biosynthesis Requires Two Highly Dedicated Triterpene Cyclases in a Fern Lycopodium clavatum.
Chembiochem : a European journal of chemical biology 17, 288-290 (Source: SUBMITTER) [PubMed:26663356]
[show Abstract]
Abe I, Abe T, Lou W, Masuoka T, Noguchi H (2007)
Site-directed mutagenesis of conserved aromatic residues in rat squalene epoxidase.
Biochemical and biophysical research communications 352, 259-263 [PubMed:17112472]
[show Abstract]
Shan H, Segura MJ, Wilson WK, Lodeiro S, Matsuda SP (2005)
Enzymatic cyclization of dioxidosqualene to heterocyclic triterpenes.
Journal of the American Chemical Society 127, 18008-18009 [PubMed:16366544]
[show Abstract]
Last Modified
26 March 2024