CHEBI:66645 - maackiapterocarpan A

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ChEBI Name maackiapterocarpan A
ChEBI ID CHEBI:66645
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H20O6
Net Charge 0
Average Mass 368.37990
Monoisotopic Mass 368.12599
InChI InChI=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
InChIKey XVIZOEGEWDVLRY-FKIZINRSSA-N
SMILES [H][C@@]12COc3cc(O)c4OC(C)(C)CCc4c3[C@]1([H])Oc1cc3OCOc3cc21
Metabolite of Species Details
Maackia amurensis (NCBI:txid37501) Found in stem (BTO:0001300). Previous component: stem bark; See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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]-pterocarpan ChEBI
Manual Xref Database
CN101434592 Patent
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Registry Number Type Source
19598945 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
19252325 PubMed citation Europe PMC
Last Modified
16 January 2014