beta-lapachone (CHEBI:10429)

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ChEBI Name	β-lapachone

ChEBI ID	CHEBI:10429

ChEBI ASCII Name	beta-lapachone

Definition	A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.

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

Secondary ChEBI IDs	CHEBI:66546

Supplier Information

Download	Molfile XML SDF

Formula

C15H14O3

Net Charge

Average Mass

242.26990

Monoisotopic Mass

242.09429

InChI

InChI=1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3

InChIKey

QZPQTZZNNJUOLS-UHFFFAOYSA-N

SMILES

CC1(C)CCC2=C(O1)c1ccccc1C(=O)C2=O

Metabolite of Species	Details
Tabebuia avellanedae (IPNI:110853-1)	Found in bark (BTO:0001301). See: PubMed

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.

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	β-lapachone (CHEBI:10429) has role anti-inflammatory agent (CHEBI:67079) β-lapachone (CHEBI:10429) has role antineoplastic agent (CHEBI:35610) β-lapachone (CHEBI:10429) has role plant metabolite (CHEBI:76924) β-lapachone (CHEBI:10429) is a benzochromenone (CHEBI:64986) β-lapachone (CHEBI:10429) is a orthoquinones (CHEBI:25622)

IUPAC Name

2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

Synonyms	Sources
3,4-dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione	ChEBI
ARQ 501	ChemIDplus
β-lap	ChEBI
beta-Lapachone	KEGG COMPOUND

Last Modified

03 June 2016