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CHEBI:65979 - graminone B

ChEBI IDCHEBI:65979
ChEBI Namegraminone B
Stars
DefinitionA lignan that is tetrahydro-1H,3H-furo[3,4-c]furan-1-one substituted by a 3-hydroxy-4,5-dimethoxyphenyl at position 3 and a 3-hydroxy-4,5-dimethoxyphenyl group at position 5. Isolated from the rhizomes of Imperata cylindrica, it exhibits vasodilative activity.
Last Modified8 February 2013
DownloadsMolfile
FormulaC21H22O8
Net Charge0
Average Mass402.399
Monoisotopic Mass402.13147
SMILES[H][C@@]12CO[C@@H](c3cc(O)cc(OC)c3)[C@]1([H])C(=O)O[C@H]2c1cc(O)c(OC)c(OC)c1
InChIInChI=1S/C21H22O8/c1-25-13-5-10(4-12(22)8-13)19-17-14(9-28-19)18(29-21(17)24)11-6-15(23)20(27-3)16(7-11)26-2/h4-8,14,17-19,22-23H,9H2,1-3H3/t14-,17-,18+,19+/m1/s1
InChIKeyJTDVCRMQMDJLOR-OAOYMFHYSA-N
Species of MetaboliteComponentSourceComments
Imperata cylindrica (ncbitaxon:80369) rhizome (BTO:0001181) PubMed (7714541)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
vasodilator agent  A drug used to cause dilation of the blood vessels.
ChEBI Ontology
Outgoing Relation(s)
graminone B (CHEBI:65979) has role metabolite (CHEBI:25212)
graminone B (CHEBI:65979) has role vasodilator agent (CHEBI:35620)
graminone B (CHEBI:65979) is a lignan (CHEBI:25036)
graminone B (CHEBI:65979) is a methoxybenzenes (CHEBI:51683)
graminone B (CHEBI:65979) is a phenols (CHEBI:33853)
graminone B (CHEBI:65979) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3R,3aS,6R,6aR)-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-(3-hydroxy-5-methoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-one
Registry NumbersSources
Reaxys:22818843Reaxys
Citations