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CHEBI:66369 - 3-O-methylcalopocarpin

ChEBI IDCHEBI:66369
ChEBI Name3-O-methylcalopocarpin
Stars
ASCII Name3-O-methylcalopocarpin
DefinitionA member of the class of pterocarpans that is (6aR,11aR)-pterocarpan substituted by a hydroxy group at position 9, a methoxy group at position 3 and a prenyl group at position 2. Isolated from Erythrina glauca and Erythrina burttii, it exhibits anti-HIV activity.
Last Modified16 January 2014
DownloadsMolfile
FormulaC21H22O4
Net Charge0
Average Mass338.403
Monoisotopic Mass338.15181
SMILES[H][C@@]12COc3cc(OC)c(CC=C(C)C)cc3[C@]1([H])Oc1cc(O)ccc12
InChIInChI=1S/C21H22O4/c1-12(2)4-5-13-8-16-19(10-18(13)23-3)24-11-17-15-7-6-14(22)9-20(15)25-21(16)17/h4,6-10,17,21-22H,5,11H2,1-3H3/t17-,21-/m0/s1
InChIKeyFZFGGNNUYSILSL-UWJYYQICSA-N
Species of MetaboliteComponentSourceComments
Erythrina burttii (IPNI:494372-1) stem (BTO:0001300) PubMed (12770595) Previous component: stem bark;
Erythrina glauca (IPNI:494436-1) bark (BTO:0001301) PubMed (9170286)
Roles Classification
Biological Roles:
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
3-O-methylcalopocarpin (CHEBI:66369) has functional parent (6aR,11aR)-pterocarpan (CHEBI:73133)
3-O-methylcalopocarpin (CHEBI:66369) has role anti-HIV agent (CHEBI:64946)
3-O-methylcalopocarpin (CHEBI:66369) has role plant metabolite (CHEBI:76924)
3-O-methylcalopocarpin (CHEBI:66369) is a aromatic ether (CHEBI:35618)
3-O-methylcalopocarpin (CHEBI:66369) is a phenols (CHEBI:33853)
3-O-methylcalopocarpin (CHEBI:66369) is a pterocarpans (CHEBI:26377)
IUPAC Name 
(6aR,11aR)-3-methoxy-2-(3-methylbut-2-en-1-yl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-9-ol
Synonyms  Source
9-hydroxy-3-methoxy-2-prenylpterocarpanChEBI
Orientanol BHMDB
Manual XrefsDatabases
HMDB0031633HMDB
Registry NumbersSources
Reaxys:7945641Reaxys
Citations