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CHEBI:70484 - (S)-1'-methyloctyl caffeate

Default Structure
ChEBI IDCHEBI:70484
ChEBI Name(S)-1'-methyloctyl caffeate
Stars
ASCII Name(S)-1'-methyloctyl caffeate
DefinitionAn alkyl caffeate ester obtained by the formal condensation of trans-caffeic acid with nonan-2-ol. Isolated from the leaves of Piper sanguineispicum, it has been shown to exhibit antileishmanial activity.
Last Modified15 April 2015
DownloadsMolfile
FormulaC18H26O4
Net Charge0
Average Mass306.402
Monoisotopic Mass306.18311
SMILESCCCCCCC[C@H](C)OC(=O)/C=C/c1ccc(O)c(O)c1
InChIInChI=1S/C18H26O4/c1-3-4-5-6-7-8-14(2)22-18(21)12-10-15-9-11-16(19)17(20)13-15/h9-14,19-20H,3-8H2,1-2H3/b12-10+/t14-/m0/s1
InChIKeyDEXGFPWDAXJBTA-WONIAPNHSA-N
Species of MetaboliteComponentSourceComments
Piper sanguineispicum (IPNI:199083-2) leaf (BTO:0000713) PubMed (20954722) 90% ethanolic extract of dried leaves
Roles Classification
Biological Roles:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
ChEBI Ontology
Outgoing Relation(s)
(S)-1'-methyloctyl caffeate (CHEBI:70484) has functional parent nonan-2-ol (CHEBI:78304)
(S)-1'-methyloctyl caffeate (CHEBI:70484) has role antileishmanial agent (CHEBI:70868)
(S)-1'-methyloctyl caffeate (CHEBI:70484) has role plant metabolite (CHEBI:76924)
(S)-1'-methyloctyl caffeate (CHEBI:70484) is a alkyl caffeate ester (CHEBI:65331)
IUPAC Name 
(2S)-nonan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Registry NumbersSources
Reaxys:21092027Reaxys
Citations