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CHEBI:66598 - luzonial A

ChEBI IDCHEBI:66598
ChEBI Nameluzonial A
Stars
DefinitionAn iridoid monoterpenoid that is hexahydro-1H-cyclopenta[c]furan substituted by hydroxy groups at positions 1 and 3a, a 3-oxopropen-2yl group at position 6 and a trans-4-coumaroyloxy moiety at position 4 (the 1S,3aS,4S,6S,6aS stereoisomer). Isolated from the leaves of Viburnum luzonicum, it exhibits antineoplastic activity.
Last Modified26 March 2013
DownloadsMolfile
FormulaC19H20O7
Net Charge0
Average Mass360.362
Monoisotopic Mass360.12090
SMILES[H][C@]12[C@@H](C(=C)C=O)C[C@H](OC(=O)/C=C/c3ccc(O)cc3)[C@@]1(O)CO[C@@H]2O
InChIInChI=1S/C19H20O7/c1-11(9-20)14-8-15(19(24)10-25-18(23)17(14)19)26-16(22)7-4-12-2-5-13(21)6-3-12/h2-7,9,14-15,17-18,21,23-24H,1,8,10H2/b7-4+/t14-,15+,17-,18+,19+/m1/s1
InChIKeyHJTBDPQCVMXWMZ-AQSJNEJESA-N
Species of MetaboliteComponentSourceComments
Viburnum luzonicum (IPNI:149799-1) leaf (BTO:0000713) PubMed (15635247)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
luzonial A (CHEBI:66598) has functional parent trans-4-coumaric acid (CHEBI:32374)
luzonial A (CHEBI:66598) has role antineoplastic agent (CHEBI:35610)
luzonial A (CHEBI:66598) has role metabolite (CHEBI:25212)
luzonial A (CHEBI:66598) is a aldehyde (CHEBI:17478)
luzonial A (CHEBI:66598) is a cinnamate ester (CHEBI:36087)
luzonial A (CHEBI:66598) is a cyclic ether (CHEBI:37407)
luzonial A (CHEBI:66598) is a iridoid monoterpenoid (CHEBI:50563)
luzonial A (CHEBI:66598) is a organic heterobicyclic compound (CHEBI:27171)
luzonial A (CHEBI:66598) is a phenols (CHEBI:33853)
luzonial A (CHEBI:66598) is a secondary alcohol (CHEBI:35681)
luzonial A (CHEBI:66598) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
(1S,3aS,4S,6S,6aS)-1,3a-dihydroxy-6-(3-oxoprop-1-en-2-yl)hexahydro-1H-cyclopenta[c]furan-4-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
Registry NumbersSources
Reaxys:10132479Reaxys
Citations