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

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

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ChEBI ID	CHEBI:65661
ChEBI Name	3-O-trans-p-coumaroyl actinidic acid
Stars
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.
Last Modified	17 December 2012
Downloads	Molfile

Formula	C39H52O7
Net Charge	0
Average Mass	632.838
Monoisotopic Mass	632.37130
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
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

Species of Metabolite	Component	Source	Comments
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:	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).

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 acid	ChEBI

Citations