CHEBI:65661 - 3-O-trans-p-coumaroyl actinidic acid

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ChEBI Name 3-O-trans-p-coumaroyl actinidic acid
ChEBI ID CHEBI:65661
ChEBI ASCII Name 3-O-trans-p-coumaroyl actinidic acid
Definition A pentacyclic triterpenoid that is the cinnamate ester obtained by the formal condensation of the carboxy group of trans-4-coumaric acid with the hydroxy group at position 3 of actinidic acid (the 2α,3β stereoisomer). It is isolated from the roots of Actinidia arguta and exhibits inhibitory activity towards pancreatic lipase.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C39H52O7
Net Charge 0
Average Mass 632.82600
Monoisotopic Mass 632.37130
InChI InChI=1S/C39H52O7/c1-23-15-18-39(34(44)45)20-19-37(5)27(32(39)24(23)2)12-13-30-35(3)21-28(42)33(36(4,22-40)29(35)16-17-38(30,37)6)46-31(43)14-9-25-7-10-26(41)11-8-25/h7-12,14,24,28-30,32-33,40-42H,1,13,15-22H2,2-6H3,(H,44,45)/b14-9+/t24-,28+,29+,30+,32-,33-,35-,36-,37+,38+,39-/m0/s1
InChIKey IFPMSAOPSQVFLA-VYXVHPRESA-N
SMILES [H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)C(=C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)[C@H](OC(=O)\C=C\c1ccc(O)cc1)[C@@]2(C)CO
Metabolite of Species Details
Actinidia arguta (NCBI:txid64478) Found in root (BTO:0001188). 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.
EC 3.1.1.3 (triacylglycerol lipase) inhibitor
Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of triacylglycerol lipase (EC 3.1.1.3).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 3-O-trans-p-coumaroyl actinidic acid (CHEBI:65661) has functional parent trans-4-coumaric acid (CHEBI:32374)
3-O-trans-p-coumaroyl actinidic acid (CHEBI:65661) has functional parent actinidic acid (CHEBI:71457)
3-O-trans-p-coumaroyl actinidic acid (CHEBI:65661) has role EC 3.1.1.3 (triacylglycerol lipase) inhibitor (CHEBI:65001)
3-O-trans-p-coumaroyl actinidic acid (CHEBI:65661) has role metabolite (CHEBI:25212)
3-O-trans-p-coumaroyl actinidic acid (CHEBI:65661) is a cinnamate ester (CHEBI:36087)
3-O-trans-p-coumaroyl actinidic acid (CHEBI:65661) is a hydroxy monocarboxylic acid (CHEBI:35868)
3-O-trans-p-coumaroyl actinidic acid (CHEBI:65661) is a pentacyclic triterpenoid (CHEBI:25872)
3-O-trans-p-coumaroyl actinidic acid (CHEBI:65661) is a primary alcohol (CHEBI:15734)
3-O-trans-p-coumaroyl actinidic acid (CHEBI:65661) is a secondary alcohol (CHEBI:35681)
IUPAC Name
(2α,3β)-2,23-dihydroxy-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}ursa-12,20(30)-dien-28-oic acid
Synonym Source
3β-(trans-p-coumaroyl)oxy-2α,23-dihydroxyurs-12(13),20(30)-dien-28-oic acid ChEBI
Citation Waiting for Citations Type Source
18481026 PubMed citation Europe PMC
Last Modified
17 December 2012