CHEBI:67630 - (−)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,9':7',9-diepoxylignane

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ChEBI Name (−)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,9':7',9-diepoxylignane
ChEBI ID CHEBI:67630
ChEBI ASCII Name (-)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,9':7',9-diepoxylignane
Definition A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 3,4,5-trimethoxyphenyl and a 4-hydroxy-3,5-dimethoxyphenyl group at positions 4 and 1 respectively. It has been isolated from the stems of Sinocalamus affinis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C23H28O8
Net Charge 0
Average Mass 432.46360
Monoisotopic Mass 432.17842
InChI InChI=1S/C23H28O8/c1-25-16-6-12(7-17(26-2)20(16)24)21-14-10-31-22(15(14)11-30-21)13-8-18(27-3)23(29-5)19(9-13)28-4/h6-9,14-15,21-22,24H,10-11H2,1-5H3/t14-,15-,21+,22+/m1/s1
InChIKey AJMQKDTUOKAQNT-SDVFQCAASA-N
SMILES COc1cc(cc(OC)c1O)[C@@H]1OC[C@@H]2[C@H]1CO[C@H]2c1cc(OC)c(OC)c(OC)c1
Metabolite of Species Details
Sinocalamus affinis (IPNI:421970-1) Found in stem (BTO:0001300). 95% Ethanolic extract of skin-removed, air-dried, powdered stems. 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 (−)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,9':7',9-diepoxylignane (CHEBI:67630) has role plant metabolite (CHEBI:76924)
(−)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,9':7',9-diepoxylignane (CHEBI:67630) is a furofuran (CHEBI:47790)
(−)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,9':7',9-diepoxylignane (CHEBI:67630) is a lignan (CHEBI:25036)
(−)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,9':7',9-diepoxylignane (CHEBI:67630) is a methoxybenzenes (CHEBI:51683)
(−)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,9':7',9-diepoxylignane (CHEBI:67630) is a phenols (CHEBI:33853)
IUPAC Name
2,6-dimethoxy-4-[(1R,3aS,4R,6aS)-4-(3,4,5-trimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]phenol
Registry Number Type Source
21559774 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21469695 PubMed citation Europe PMC
Last Modified
06 October 2014