EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

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

ChEBI IDCHEBI:65661
ChEBI Name3-O-trans-p-coumaroyl actinidic acid
Stars
ASCII Name3-O-trans-p-coumaroyl actinidic acid
DefinitionA 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.
Last Modified17 December 2012
DownloadsMolfile
FormulaC39H52O7
Net Charge0
Average Mass632.838
Monoisotopic Mass632.37130
SMILES[H][C@]12CC=C3[C@@](C)(CC[C@@]4(C(=O)O)CCC(=C)[C@H](C)[C@@]34[H])[C@]1(C)CC[C@]1([H])[C@]2(C)C[C@@H](O)[C@H](OC(=O)/C=C/c2ccc(O)cc2)[C@@]1(C)CO
InChIInChI=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
InChIKeyIFPMSAOPSQVFLA-VYXVHPRESA-N
Species of MetaboliteComponentSourceComments
Actinidia arguta (ncbitaxon:64478) root (BTO:0001188) PubMed (18481026)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
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 acidChEBI
Citations