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3-(Z)-caffeoyllupeol

Go to external page http://purl.obolibrary.org/obo/CHEBI_65549

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.

Term info

Label

3-(Z)-caffeoyllupeol

Synonyms
  • (3beta)-lup-20(29)-en-3-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate
database cross reference
Subsets

3_STAR

IUPAC NAME
(3beta)-lup-20(29)-en-3-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate [ IUPAC ]

charge

0

formula

C39H56O4

has obo namespace

chebi_ontology

id

CHEBI:65549

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

mass

588.85950

monoisotopicmass

588.41786

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]