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CHEBI:65663 - 3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid

ChEBI IDCHEBI:65663
ChEBI Name3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid
Stars
ASCII Name3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid
DefinitionA pentacyclic triterpenoid that is the cinnamate ester obtained by the formal condensation of trans-4-coumaric acid with D:C-friedoolean-7,9(11)-dien-3β-ol-29-oic acid. It is isolated from the stems of Lagenaria siceraria and exhibits cytotoxic activity against human hepatoma SK-Hep 1 cells.
Last Modified17 December 2012
DownloadsMolfile
FormulaC39H52O5
Net Charge0
Average Mass600.840
Monoisotopic Mass600.38147
SMILES[H][C@@]12C[C@](C)(C(=O)O)CC[C@]1(C)CC[C@]1(C)C3=CC[C@@]4([H])C(C)(C)[C@@H](OC(=O)/C=C/c5ccc(O)cc5)CC[C@]4(C)C3=CC[C@@]21C
InChIInChI=1S/C39H52O5/c1-34(2)29-14-13-28-27(37(29,5)18-17-31(34)44-32(41)15-10-25-8-11-26(40)12-9-25)16-19-39(7)30-24-36(4,33(42)43)21-20-35(30,3)22-23-38(28,39)6/h8-13,15-16,29-31,40H,14,17-24H2,1-7H3,(H,42,43)/b15-10+/t29-,30+,31-,35+,36+,37+,38+,39-/m0/s1
InChIKeyNOTQCQMXZCILJE-WYGBHMDXSA-N
Species of MetaboliteComponentSourceComments
Lagenaria siceraria (ncbitaxon:3668) stem (BTO:0001300) PubMed (18310955)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
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)
3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (CHEBI:65663) has functional parent trans-4-coumaric acid (CHEBI:32374)
3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (CHEBI:65663) has functional parent D:C-friedoolean-7,9(11)-dien-3β-ol-29-oic acid (CHEBI:71468)
3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (CHEBI:65663) has role antineoplastic agent (CHEBI:35610)
3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (CHEBI:65663) has role metabolite (CHEBI:25212)
3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (CHEBI:65663) is a cinnamate ester (CHEBI:36087)
3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (CHEBI:65663) is a monocarboxylic acid (CHEBI:25384)
3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (CHEBI:65663) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name 
(2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydropicene-2-carboxylic acid
Registry NumbersSources
Reaxys:15864359Reaxys
Citations