lapachol (CHEBI:6377)

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ChEBI Name	lapachol

ChEBI ID	CHEBI:6377

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C15H14O3

Net Charge

Average Mass

242.274

Monoisotopic Mass

242.09429

InChI

InChI=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

InChIKey

CIEYTVIYYGTCCI-UHFFFAOYSA-N

SMILES

CC(C)=CCC1=C(O)C(=O)C2=C(C=CC=C2)C1=O

Metabolite of Species	Details
Tabebuia avellanedae (IPNI:110853-1)	See: DOI
Abutilon pakistanicum (IPNI:323558-2)	Found in whole plant (BTO:0001461). See: DOI

Roles Classification
Biological Role(s):	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.

Application(s):	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	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	Sources
2-hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthalenedione	ChEBI
2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione	ChEBI
2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone	ChemIDplus
2-hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione	ChEBI
Bethabarra wood	ChemIDplus
C.I. 75490	ChemIDplus
C.I. natural yellow 16	ChemIDplus
greenhartin	ChemIDplus
Ipe-tobacco wood	ChemIDplus
Lapachol	KEGG COMPOUND
lapachol wood	ChemIDplus
Surinam greenheart wood	ChemIDplus
Taigu wood	ChemIDplus
taiguic acid	ChemIDplus
tecomin	ChemIDplus

Last Modified

13 October 2021