(+)-sesamin dicatechol (CHEBI:136543)

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ChEBI Name	(+)-sesamin dicatechol

ChEBI ID	CHEBI:136543

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Kristian Axelsen

Supplier Information

Download	Molfile XML SDF

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Formula

C18H18O6

Net Charge

Average Mass

330.333

Monoisotopic Mass

330.11034

InChI

InChI=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

InChIKey

OQSOTSIYXPYTRE-YDOWWZDFSA-N

SMILES

C1=C(C(=CC(=C1)[C@]2(OC[C@]3([C@@]2(CO[C@@]3(C4=CC=C(C(=C4)O)O)[H])[H])[H])[H])O)O

Metabolite of Species	Details
Morinda citrifolia (NCBI:txid43522)	Methanol extract 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.

ChEBI Ontology
Outgoing	(+)-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

Registry Number	Type	Source
9658635	Reaxys Registry Number	Reaxys

Last Modified

26 January 2023