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ONTOLOGY REPORT - ANNOTATIONS


Term:3-(Z)-caffeoyllupeol
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Accession:CHEBI:65549 term browser browse the term
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 3beta stereoisomer). It is isolated from the fruits of Bruguiera parviflora and exhibits antimalarial activity.
Synonyms:exact_synonym: (3beta)-lup-20(29)-en-3-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate
 related_synonym: Formula=C39H56O4;   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]
 xref: PMID:15635238 "Europe PMC";   Reaxys:10050764 "Reaxys"


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  CHEBI ontology 19734
    role 19680
      biological role 19678
        biochemical role 19177
          metabolite 19147
            3-(Z)-caffeoyllupeol 0
Path 2
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  CHEBI ontology 19734
    subatomic particle 19730
      composite particle 19730
        hadron 19730
          baryon 19730
            nucleon 19730
              atomic nucleus 19730
                atom 19730
                  main group element atom 19614
                    p-block element atom 19614
                      carbon group element atom 19506
                        carbon atom 19500
                          organic molecular entity 19500
                            organic group 18414
                              organic divalent group 18406
                                organodiyl group 18406
                                  carbonyl group 18295
                                    carbonyl compound 18295
                                      carboxylic acid 17963
                                        monocarboxylic acid 17265
                                          alpha,beta-unsaturated monocarboxylic acid 11350
                                            cinnamic acids 2359
                                              hydroxycinnamic acid 1239
                                                caffeic acid 541
                                                  cis-caffeic acid 113
                                                    3-(Z)-caffeoyllupeol 0
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