Chemical substance record

Lapachol

84-79-7C₁₅H₁₄O₃242.274 g/mol

Organic/Inorganic Small MoleculeChEBI source record

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. — ChEBI

Safety references

Safety documents & references

Supplier matching matters

Find the safety document for your specific supplier, product number and grade.

Find a product-specific SDS

Search SDS PDFs Sigma-Aldrich Thermo Fisher

Safety guides and government classification records are not a manufacturer’s SDS. Match supplier, product number, concentration, physical form, region and revision before using a document.

Identity & molecular properties

Source-linked values

CAS number	84-79-7	ChEBI ↗
Molecular formula	C₁₅H₁₄O₃	ChEBI ↗
Molar mass	242.274 g/mol	ChEBI ↗
Monoisotopic mass	242.09429 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:6377	ChEBI ↗

Names & structural identifiers

Copy any identifier

Source preferred name

lapachol

IUPAC name

2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione

InChIKey

CIEYTVIYYGTCCI-UHFFFAOYSA-N

SMILES

CC(C)=CCC1=C(O)C(=O)c2ccccc2C1=O

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

Names & synonyms

2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

hydroxy-1,4-naphthoquinoneChEBI parent class · 132157 ↗olefinic compoundChEBI parent class · 78840 ↗

ketone organic molecular entity

Roles recorded in ChEBI

antibacterial agentantineoplastic agentanti-inflammatory agentplant metabolite

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00412756 mol

Uses 242.274 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 15 atoms

74.36%

O

Oxygen · 3 atoms

19.81%

H

Hydrogen · 14 atoms

5.82%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

In vitro and in vivo Leishmanicidal activity of 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (lapachol). ↗Phytotherapy research : PTR · 2001 Feb · PMID 11180522

Efficacy of lapachol on treatment of cutaneous and visceral leishmaniasis. ↗Experimental parasitology · 2019 Apr · PMID 30797783

Search PubMed Google Scholar

Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:6377

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

How this record was assembled Suggest a correction