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

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:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
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