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CHEBI:66600 - luzonidial B

ChEBI IDCHEBI:66600
ChEBI Nameluzonidial B
Stars
DefinitionAn iridoid monoterpenoid that is cyclopentene substituted by a formyl group at position 3, a hydroxymethyl group at position 2, 3-oxopropen-2yl group at position 4 and a cis-4-coumaroyloxy moiety at position 1 (the 1S,4R stereoisomer). Isolated from the leaves of Viburnum luzonicum, it exhibits antineoplastic activity.
Last Modified26 March 2013
DownloadsMolfile
FormulaC19H18O6
Net Charge0
Average Mass342.347
Monoisotopic Mass342.11034
SMILESC=C(C=O)[C@H]1C[C@H](OC(=O)/C=C\c2ccc(O)cc2)C(CO)=C1C=O
InChIInChI=1S/C19H18O6/c1-12(9-20)15-8-18(17(11-22)16(15)10-21)25-19(24)7-4-13-2-5-14(23)6-3-13/h2-7,9-10,15,18,22-23H,1,8,11H2/b7-4-/t15-,18+/m1/s1
InChIKeyIOKUHHOVWITKLG-DYKRAQSHSA-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)
luzonidial B (CHEBI:66600) has functional parent cis-4-coumaric acid (CHEBI:17450)
luzonidial B (CHEBI:66600) has role antineoplastic agent (CHEBI:35610)
luzonidial B (CHEBI:66600) has role metabolite (CHEBI:25212)
luzonidial B (CHEBI:66600) is a aldehyde (CHEBI:17478)
luzonidial B (CHEBI:66600) is a cinnamate ester (CHEBI:36087)
luzonidial B (CHEBI:66600) is a iridoid monoterpenoid (CHEBI:50563)
luzonidial B (CHEBI:66600) is a phenols (CHEBI:33853)
IUPAC Name 
(1S,4R)-3-formyl-2-(hydroxymethyl)-4-(3-oxoprop-1-en-2-yl)cyclopent-2-en-1-yl (2Z)-3-(4-hydroxyphenyl)prop-2-enoate
Registry NumbersSources
Reaxys:10129766Reaxys
Citations