CHEBI:66470 - (+)-sesamin

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ChEBI Name (+)-sesamin
ChEBI ID CHEBI:66470
Definition A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H18O6
Net Charge 0
Average Mass 354.354
Monoisotopic Mass 354.11034
InChI InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1
InChIKey PEYUIKBAABKQKQ-AFHBHXEDSA-N
SMILES [C@]12([C@@]([C@H](OC1)C3=CC4=C(C=C3)OCO4)(CO[C@@H]2C5=CC6=C(C=C5)OCO6)[H])[H]
Metabolite of Species Details
Hypericum chinense (IPNI:433315-1) Found in leaf (BTO:0000713). 95% EtOH extract of dried, chopped leaves See: PubMed
Cinnamomum camphora (NCBI:txid13429) Found in stem (BTO:0001300). See: NAT PROD COMMUN, 2006, 1, 21
Piper sarmentosum (NCBI:txid405319) Found in leaf (BTO:0000713). Chloroform soluble extract of aerial parts(leaves, twigs, stems, inflorescence) See: PubMed
Piper sarmentosum (NCBI:txid405319) Found in stem (BTO:0001300). Chloroform soluble extract of aerial parts(leaves, twigs, stems, inflorescence) See: PubMed
Piper sarmentosum (NCBI:txid405319) Found in twig (BTO:0001411). Chloroform soluble extract of aerial parts(leaves, twigs, stems, inflorescence) See: PubMed
Piper sarmentosum (NCBI:txid405319) Found in inflorescence (BTO:0000628). Chloroform soluble extract of aerial parts(leaves, twigs, stems, inflorescence) 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.
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing (+)-sesamin (CHEBI:66470) has role antineoplastic agent (CHEBI:35610)
(+)-sesamin (CHEBI:66470) has role neuroprotective agent (CHEBI:63726)
(+)-sesamin (CHEBI:66470) has role plant metabolite (CHEBI:76924)
(+)-sesamin (CHEBI:66470) is a benzodioxoles (CHEBI:38298)
(+)-sesamin (CHEBI:66470) is a furofuran (CHEBI:47790)
(+)-sesamin (CHEBI:66470) is a lignan (CHEBI:25036)
Incoming (+)-sesamin dicatechol (CHEBI:136543) has functional parent (+)-sesamin (CHEBI:66470)
(+)-sesamin monocatechol (CHEBI:136542) has functional parent (+)-sesamin (CHEBI:66470)
IUPAC Name
5,5'-(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(1,3-benzodioxole)
Synonyms Sources
(+)-sesamin UniProt
Fagarol ChemIDplus
Sezamin ChemIDplus
Manual Xrefs Databases
C00000601 KNApSAcK
C10882 KEGG COMPOUND
CPD-8922 MetaCyc
HMDB0034256 HMDB
Sesamin Wikipedia
View more database links
Registry Numbers Types Sources
607-80-7 CAS Registry Number KEGG COMPOUND
607-80-7 CAS Registry Number ChemIDplus
96118 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16309310 PubMed citation Europe PMC
16785429 PubMed citation Europe PMC
21043475 PubMed citation Europe PMC
21973101 PubMed citation Europe PMC
27558960 PubMed citation Europe PMC
27632923 PubMed citation Europe PMC
28157651 PubMed citation Europe PMC
28239780 PubMed citation Europe PMC
Last Modified
13 June 2018
General Comment
2012-07-27 NAT PROD COMMUN, 2006, 1, 21