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

ChEBI IDCHEBI:65662
ChEBI Name2-O-E-p-coumaroyl alphitolic acid
Stars
ASCII Name2-O-E-p-coumaroyl alphitolic acid
DefinitionA 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.
Last Modified1 June 2015
DownloadsMolfile
FormulaC39H54O6
Net Charge0
Average Mass618.855
Monoisotopic Mass618.39204
SMILES[H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4(C(=O)O)CC[C@@H](C(=C)C)[C@@]43[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O)[C@H](OC(=O)/C=C/c3ccc(O)cc3)C[C@]21C
InChIInChI=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
InChIKeyLCHMSLHVXVQJDG-GLDUGTPFSA-N
Species of MetaboliteComponentSourceComments
Zizyphus jujuba (ncbitaxon:326968) fruit (BTO:0000486) Article (CHEM PHARM BULL,1978,26,6,1798) Dried fruits
Ziziphus cambodianus (IPNI:719271-1) root (BTO:0001188) PubMed (16595959) Previous component: root bark;
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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:
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.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:10410488Reaxys
Citations