CHEBI:66369 - 3-O-methylcalopocarpin

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ChEBI Name 3-O-methylcalopocarpin
ChEBI ID CHEBI:66369
ChEBI ASCII Name 3-O-methylcalopocarpin
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C21H22O4
Net Charge 0
Average Mass 338.39700
Monoisotopic Mass 338.15181
InChI InChI=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
InChIKey FZFGGNNUYSILSL-UWJYYQICSA-N
SMILES [H][C@@]12COc3cc(OC)c(CC=C(C)C)cc3[C@]1([H])Oc1cc(O)ccc21
Metabolite of Species Details
Erythrina burttii (IPNI:494372-1) Found in stem (BTO:0001300). Previous component: stem bark; See: PubMed
Erythrina glauca (IPNI:494436-1) Found in bark (BTO:0001301). See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
9-hydroxy-3-methoxy-2-prenylpterocarpan ChEBI
Orientanol B HMDB
Manual Xref Database
HMDB0031633 HMDB
View more database links
Registry Number Type Source
7945641 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12770595 PubMed citation Europe PMC
9170286 PubMed citation Europe PMC
Last Modified
16 January 2014