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CHEBI:66165 - sandwicensin

Default Structure
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 × bidwillii (IPNI:494362-1) - DOI (10.1016/S0031-9422(97)00732-2)
Erythrina glauca (IPNI:494436-1) bark (BTO:0001301) PubMed (9170286)
Erythrina lysistemon (ncbitaxon:347910)
flower (BTO:0000469) Article (PROCEEDINGS OF THE 11TH NAPRECA SYMPOSIUM,AUGUST 9-12,ANTANANARIVO,MADAGASCAR,2005,97-109)
aerial part (BTO:0001658) Article (PROCEEDINGS OF THE 11TH NAPRECA SYMPOSIUM,AUGUST 9-12,ANTANANARIVO,MADAGASCAR,2005,97-109)
Erythrina mildbraedii (IPNI:494506-1) - DOI (10.1016/0031-9422(88)80746-5)
Erythrina poeppigiana (IPNI:96637-2) root (BTO:0001188) PubMed (12803562)
Erythrina stricta (IPNI:494596-1) root (BTO:0001188) PubMed (18087807)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
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