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

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ChEBI Name 3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid
ChEBI ID CHEBI:65663
ChEBI ASCII Name 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C39H52O5
Net Charge 0
Average Mass 600.82720
Monoisotopic Mass 600.38147
InChI InChI=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
InChIKey NOTQCQMXZCILJE-WYGBHMDXSA-N
SMILES [H][C@@]12CC=C3C(=CC[C@@]4(C)[C@]5([H])C[C@@](C)(CC[C@]5(C)CC[C@]34C)C(O)=O)[C@@]1(C)CC[C@H](OC(=O)\C=C\c1ccc(O)cc1)C2(C)C
Metabolite of Species Details
Lagenaria siceraria (NCBI:txid3668) Found in stem (BTO:0001300). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
15864359 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18310955 PubMed citation Europe PMC
Last Modified
17 December 2012