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CHEBI:70482 - (S)-1'-methylbutyl caffeate

Default Structure
ChEBI IDCHEBI:70482
ChEBI Name(S)-1'-methylbutyl caffeate
Stars
ASCII Name(S)-1'-methylbutyl caffeate
DefinitionAn alkyl caffeate ester obtained by the formal condensation of trans-caffeic acid with 2-pentanol. Isolated from the leaves of Piper sanguineispicum, it has been shown to exhibit antileishmanial activity.
Last Modified15 April 2015
DownloadsMolfile
FormulaC14H18O4
Net Charge0
Average Mass250.294
Monoisotopic Mass250.12051
SMILESCCC[C@H](C)OC(=O)/C=C/c1ccc(O)c(O)c1
InChIInChI=1S/C14H18O4/c1-3-4-10(2)18-14(17)8-6-11-5-7-12(15)13(16)9-11/h5-10,15-16H,3-4H2,1-2H3/b8-6+/t10-/m0/s1
InChIKeyAGXDVPULWUXVDT-PCGIRMHASA-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'-methylbutyl caffeate (CHEBI:70482) has functional parent pentan-2-ol (CHEBI:77518)
(S)-1'-methylbutyl caffeate (CHEBI:70482) has role antileishmanial agent (CHEBI:70868)
(S)-1'-methylbutyl caffeate (CHEBI:70482) has role plant metabolite (CHEBI:76924)
(S)-1'-methylbutyl caffeate (CHEBI:70482) is a alkyl caffeate ester (CHEBI:65331)
IUPAC Name 
(2S)-pentan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Registry NumbersSources
Reaxys:21092025Reaxys
Citations