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CHEBI:66645 - maackiapterocarpan A

ChEBI IDCHEBI:66645
ChEBI Namemaackiapterocarpan A
Stars
DefinitionA member of the class of pterocarpans that is pterocarpan substituted by a hydroxy group at position 3, a methylenedioxy group across positions 8 and 9 and a 2,2-dimethyltetrahydro-2H-pyran ring fused across positions 1 and 2 (the 8aR,14aR stereoisomer). Isolated from the stem barks of Maackia amurensis,it exhibits cytotoxicity against human cancer cell lines.
Last Modified16 January 2014
DownloadsMolfile
FormulaC21H20O6
Net Charge0
Average Mass368.385
Monoisotopic Mass368.12599
SMILES[H][C@@]12COc3cc(O)c4c(c3[C@]1([H])Oc1cc3c(cc12)OCO3)CCC(C)(C)O4
InChIInChI=1S/C21H20O6/c1-21(2)4-3-10-18-17(6-13(22)19(10)27-21)23-8-12-11-5-15-16(25-9-24-15)7-14(11)26-20(12)18/h5-7,12,20,22H,3-4,8-9H2,1-2H3/t12-,20+/m0/s1
InChIKeyXVIZOEGEWDVLRY-FKIZINRSSA-N
Species of MetaboliteComponentSourceComments
Maackia amurensis (ncbitaxon:37501) stem (BTO:0001300) PubMed (19252325) Previous component: stem bark;
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
maackiapterocarpan A (CHEBI:66645) has role antineoplastic agent (CHEBI:35610)
maackiapterocarpan A (CHEBI:66645) has role plant metabolite (CHEBI:76924)
maackiapterocarpan A (CHEBI:66645) is a organic heterohexacyclic compound (CHEBI:51914)
maackiapterocarpan A (CHEBI:66645) is a phenols (CHEBI:33853)
maackiapterocarpan A (CHEBI:66645) is a pterocarpans (CHEBI:26377)
IUPAC Name 
(8aR,14aR)-3,3-dimethyl-1,2,3,8,8a,14a-hexahydro[1,3]dioxolo[5,6][1]benzofuro[3,2-c]pyrano[3,2-f]chromen-5-ol
Synonym  Source
3-hydroxy-8,9-methylenedioxy-[2',2'-dimethyl-3',4'-dihydropyrano-(5',6' : 1,2)][6aR,11aR]-pterocarpanChEBI
Manual XrefsDatabases
CN101434592Patent
Registry NumbersSources
Reaxys:19598945Reaxys
Citations