CHEBI:65549 - 3-(Z)-caffeoyllupeol

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 3-(Z)-caffeoyllupeol
ChEBI ID CHEBI:65549
ChEBI ASCII Name 3-(Z)-caffeoyllupeol
Definition A pentacyclic triterpenoid that is the cinnamate ester obtained by the formal condensation of the carboxylic group of cis-caffeic acid with the hydroxy group of lupeol (the 3β stereoisomer). It is isolated from the fruits of Bruguiera parviflora and exhibits antimalarial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C39H56O4
Net Charge 0
Average Mass 588.85950
Monoisotopic Mass 588.41786
InChI InChI=1S/C39H56O4/c1-24(2)26-15-18-36(5)21-22-38(7)27(34(26)36)11-13-31-37(6)19-17-32(35(3,4)30(37)16-20-39(31,38)8)43-33(42)14-10-25-9-12-28(40)29(41)23-25/h9-10,12,14,23,26-27,30-32,34,40-41H,1,11,13,15-22H2,2-8H3/b14-10-/t26-,27+,30-,31+,32-,34+,36+,37-,38+,39+/m0/s1
InChIKey NIKLINODNHPPMX-JPXCXHODSA-N
SMILES [H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](OC(=O)\C=C/c5ccc(O)c(O)c5)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@@]1(C)CC[C@@H](C(C)=C)[C@]21[H]
Metabolite of Species Details
Bruguiera parviflora (NCBI:txid106618) Found in fruit (BTO:0000486). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Application(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 3-(Z)-caffeoyllupeol (CHEBI:65549) has functional parent cis-caffeic acid (CHEBI:17395)
3-(Z)-caffeoyllupeol (CHEBI:65549) has functional parent lupeol (CHEBI:6570)
3-(Z)-caffeoyllupeol (CHEBI:65549) has parent hydride lupane (CHEBI:36485)
3-(Z)-caffeoyllupeol (CHEBI:65549) has role antimalarial (CHEBI:38068)
3-(Z)-caffeoyllupeol (CHEBI:65549) has role metabolite (CHEBI:25212)
3-(Z)-caffeoyllupeol (CHEBI:65549) is a catechols (CHEBI:33566)
3-(Z)-caffeoyllupeol (CHEBI:65549) is a cinnamate ester (CHEBI:36087)
3-(Z)-caffeoyllupeol (CHEBI:65549) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name
(3β)-lup-20(29)-en-3-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Registry Number Type Source
10050764 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15635238 PubMed citation Europe PMC
Last Modified
30 November 2012