EMBL-EBI | Chemical Biology | ChEBI

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

CHEBI:65549 - 3-(Z)-caffeoyllupeol

ChEBI IDCHEBI:65549
ChEBI Name3-(Z)-caffeoyllupeol
Stars
ASCII Name3-(Z)-caffeoyllupeol
DefinitionA 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.
Last Modified30 November 2012
DownloadsMolfile
FormulaC39H56O4
Net Charge0
Average Mass588.873
Monoisotopic Mass588.41786
SMILES[H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4(C)CC[C@@H](C(=C)C)[C@@]43[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](OC(=O)/C=C\c3ccc(O)c(O)c3)CC[C@]21C
InChIInChI=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
InChIKeyNIKLINODNHPPMX-JPXCXHODSA-N
Species of MetaboliteComponentSourceComments
Bruguiera parviflora (ncbitaxon:106618) fruit (BTO:0000486) PubMed (15635238)
Roles Classification
Biological Roles:
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:
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.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:10050764Reaxys
Citations