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CHEBI:66165 - sandwicensin

ChEBI IDCHEBI:66165
ChEBI Namesandwicensin
Stars
DefinitionA member of the class of pterocarpans that is (6aR,11aR)-pterocarpan substituted by a hydroxy group at position 3, a methoxy group at position 9 and a prenyl group at position 10. Isolated from Erythrina glauca and Erythrina stricta, it exhibits anti-HIV-1 activity.
Last Modified25 April 2013
DownloadsMolfile
FormulaC21H22O4
Net Charge0
Average Mass338.403
Monoisotopic Mass338.15181
SMILES[H][C@@]12COc3cc(O)ccc3[C@]1([H])Oc1c2ccc(OC)c1CC=C(C)C
InChIInChI=1S/C21H22O4/c1-12(2)4-6-15-18(23-3)9-8-14-17-11-24-19-10-13(22)5-7-16(19)21(17)25-20(14)15/h4-5,7-10,17,21-22H,6,11H2,1-3H3/t17-,21-/m0/s1
InChIKeyZFUZIYGRFSXEIQ-UWJYYQICSA-N
Species of MetaboliteComponentSourceComments
Erythrina lysistemon (ncbitaxon:347910)
aerial part (BTO:0001658) Article (PROCEEDINGS OF THE 11TH NAPRECA SYMPOSIUM,AUGUST 9-12,ANTANANARIVO,MADAGASCAR,2005,97-109)
flower (BTO:0000469) Article (PROCEEDINGS OF THE 11TH NAPRECA SYMPOSIUM,AUGUST 9-12,ANTANANARIVO,MADAGASCAR,2005,97-109)
Erythrina stricta (IPNI:494596-1) root (BTO:0001188) PubMed (18087807)
Erythrina poeppigiana (IPNI:96637-2) root (BTO:0001188) PubMed (12803562)
Erythrina × bidwillii (IPNI:494362-1) - DOI (10.1016/S0031-9422(97)00732-2)
Erythrina mildbraedii (IPNI:494506-1) - DOI (10.1016/0031-9422(88)80746-5)
Erythrina glauca (IPNI:494436-1) bark (BTO:0001301) PubMed (9170286)
Roles Classification
Biological Roles:
anti-HIV-1 agent  An anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
sandwicensin (CHEBI:66165) has role anti-HIV-1 agent (CHEBI:64947)
sandwicensin (CHEBI:66165) has role metabolite (CHEBI:25212)
sandwicensin (CHEBI:66165) is a aromatic ether (CHEBI:35618)
sandwicensin (CHEBI:66165) is a phenols (CHEBI:33853)
sandwicensin (CHEBI:66165) is a pterocarpans (CHEBI:26377)
IUPAC Name 
(6aR,11aR)-9-methoxy-10-(3-methylbut-2-en-1-yl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol
Synonym  Source
3-hydroxy-9-methoxy-10-prenylpterocarpanChEBI
Manual XrefsDatabases
LMPK12070013LIPID MAPS
Registry NumbersSources
Reaxys:9220627Reaxys
Citations