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CHEBI:136543 - (+)-sesamin dicatechol

ChEBI IDCHEBI:136543
ChEBI Name(+)-sesamin dicatechol
Stars
DefinitionA furofuran that is (+)-sesamin in which both of the methylene acetals groups have been hydrolysed to afford the corresponding bis-catechol. Found as a product of (+)-sesamin in rat liver homogenate and also produced from sesamin by an enzyme (SesA) found in Sinomonas species. no. 22 growing on sesamin.
Last Modified26 January 2023
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC18H18O6
Net Charge0
Average Mass330.336
Monoisotopic Mass330.11034
SMILES[H][C@]12CO[C@]([H])(c3ccc(O)c(O)c3)[C@@]1([H])CO[C@]2([H])c1ccc(O)c(O)c1
InChIInChI=1S/C18H18O6/c19-13-3-1-9(5-15(13)21)17-11-7-24-18(12(11)8-23-17)10-2-4-14(20)16(22)6-10/h1-6,11-12,17-22H,7-8H2/t11-,12-,17+,18+/m0/s1
InChIKeyOQSOTSIYXPYTRE-YDOWWZDFSA-N
Species of MetaboliteComponentSourceComments
Morinda citrifolia (ncbitaxon:43522) - PubMed (24224843) Methanol extract
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
(+)-sesamin dicatechol (CHEBI:136543) has functional parent (+)-sesamin (CHEBI:66470)
(+)-sesamin dicatechol (CHEBI:136543) has functional parent (+)-sesamin monocatechol (CHEBI:136542)
(+)-sesamin dicatechol (CHEBI:136543) has role plant metabolite (CHEBI:76924)
(+)-sesamin dicatechol (CHEBI:136543) is a catechols (CHEBI:33566)
(+)-sesamin dicatechol (CHEBI:136543) is a furofuran (CHEBI:47790)
(+)-sesamin dicatechol (CHEBI:136543) is a lignan (CHEBI:25036)
IUPAC Name 
4-[(1S,3aR,4S,6aR)-4-(3,4-dihydroxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]benzene-1,2-diol
Synonym  Source
SC-2ChEBI
UniProt Name  Source
(+)-sesamin dicatecholUniProt
Registry NumbersSources
Reaxys:9658635Reaxys
Citations