CHEBI:65662 - 2-O-E-p-coumaroyl alphitolic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 2-O-E-p-coumaroyl alphitolic acid
ChEBI ID CHEBI:65662
ChEBI ASCII Name 2-O-E-p-coumaroyl alphitolic acid
Definition A pentacyclic triterpenoid that is lup-20(29)-en-28-oic acid substituted by a hydroxy group at position 3 and a [(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy group at position 2 (the 2α,3β-stereoisomer ). It has been isolated from the root bark of Zizyphus jujuba and Ziziphus cambodianus.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C39H54O6
Net Charge 0
Average Mass 618.84250
Monoisotopic Mass 618.39204
InChI InChI=1S/C39H54O6/c1-23(2)26-16-19-39(34(43)44)21-20-37(6)27(32(26)39)13-14-30-36(5)22-28(33(42)35(3,4)29(36)17-18-38(30,37)7)45-31(41)15-10-24-8-11-25(40)12-9-24/h8-12,15,26-30,32-33,40,42H,1,13-14,16-22H2,2-7H3,(H,43,44)/b15-10+/t26-,27+,28+,29-,30+,32+,33-,36-,37+,38+,39-/m0/s1
InChIKey LCHMSLHVXVQJDG-GLDUGTPFSA-N
SMILES CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)C[C@@H](OC(=O)\C=C\c6ccc(O)cc6)[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O
Metabolite of Species Details
Ziziphus cambodianus (IPNI:719271-1) Found in root (BTO:0001188). Previous component: root bark; See: PubMed
Zizyphus jujuba (NCBI:txid326968) Found in fruit (BTO:0000486). Dried fruits See: CHEM PHARM BULL,1978,26,6,1798
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): antiplasmodial drug
An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antiplasmodial drug
An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 2-O-E-p-coumaroyl alphitolic acid (CHEBI:65662) has parent hydride lupane (CHEBI:36485)
2-O-E-p-coumaroyl alphitolic acid (CHEBI:65662) has role antiplasmodial drug (CHEBI:64915)
2-O-E-p-coumaroyl alphitolic acid (CHEBI:65662) has role plant metabolite (CHEBI:76924)
2-O-E-p-coumaroyl alphitolic acid (CHEBI:65662) is a cinnamate ester (CHEBI:36087)
2-O-E-p-coumaroyl alphitolic acid (CHEBI:65662) is a hydroxy monocarboxylic acid (CHEBI:35868)
2-O-E-p-coumaroyl alphitolic acid (CHEBI:65662) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name
(2α,3β)-3-hydroxy-2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}lup-20(29)-en-28-oic acid
Registry Number Type Source
10410488 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
16595959 PubMed citation Europe PMC
Last Modified
01 June 2015
General Comment
2012-07-27 CHEM PHARM BULL,1978,26,6,1798