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CHEBI:6377 - lapachol

Default Structure
ChEBI IDCHEBI:6377
ChEBI Namelapachol
Stars
DefinitionA hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae.
Last Modified13 October 2021
DownloadsMolfile
FormulaC15H14O3
Net Charge0
Average Mass242.274
Monoisotopic Mass242.09429
SMILESCC(C)=CCC1=C(O)C(=O)c2ccccc2C1=O
InChIInChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,18H,8H2,1-2H3
InChIKeyCIEYTVIYYGTCCI-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Abutilon pakistanicum (IPNI:323558-2) whole plant (BTO:0001461) DOI (10.1002/hlca.201000075)
Tabebuia avellanedae (IPNI:110853-1) - DOI (10.3998/ark.5550190.0008.204)
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.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
lapachol (CHEBI:6377) has role anti-inflammatory agent (CHEBI:67079)
lapachol (CHEBI:6377) has role antibacterial agent (CHEBI:33282)
lapachol (CHEBI:6377) has role antineoplastic agent (CHEBI:35610)
lapachol (CHEBI:6377) has role plant metabolite (CHEBI:76924)
lapachol (CHEBI:6377) is a hydroxy-1,4-naphthoquinone (CHEBI:132157)
lapachol (CHEBI:6377) is a olefinic compound (CHEBI:78840)
IUPAC Name 
2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione
Synonyms  Source
2-hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthalenedioneChEBI
2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedioneChEBI
2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinoneChemIDplus
2-hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dioneChEBI
Bethabarra woodChemIDplus
C.I. 75490ChemIDplus
Manual XrefsDatabases
10770962ChemSpider
C00002835KNApSAcK
C10366KEGG COMPOUND
HMDB0253978HMDB
LapacholWikipedia
Registry NumbersSources
CAS:84-79-7NIST Chemistry WebBook
CAS:84-79-7ChemIDplus
Citations