Structure via PubChem · Public domain (PubChem)
lapachol
Sign in to saveLapachol is a natural phenolic compound isolated from the bark of the lapacho tree. This tree is known botanically as Handroanthus impetiginosus, but was formerly known by various other botanical names such as Tabebuia avellanedae. Lapachol is also found in other species of Handroanthus.
In the Vinony graph
Within Vinony's link graph, lapachol is referenced by 17 other articles, and connects out to nature, binomial nomenclature and digital object identifier.
It is catalogued under topics including 1,4-Naphthoquinones, Chembox image size set and ECHA InfoCard ID from Wikidata.
Its subject is documented across 13 Wikipedia language editions.
Chemical data
- Formula
- C15H14O3
- Molecular weight
- 242.27 g/mol
- IUPAC name
- 4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
- SMILES
- CC(=CCC1=C(C2=CC=CC=C2C(=O)C1=O)O)C
- InChIKey
- CWPGNVFCJOPXFB-UHFFFAOYSA-N
- XLogP
- 2.8
- Polar surface area
- 54.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
314 papers- Lapachol and lapachone analogs: a journey of two decades of patent research(1997-2016).Expert opinion on therapeutic patents · 2017
- Plant-Derived Lapachol Analogs as Selective Metalloprotease Inhibitors Against Bothrops Venom: A Review.International journal of molecular sciences · 2025
- Lapachol acetylglycosylation enhances its cytotoxic and pro-apoptotic activities in HL60 cells.Toxicology in vitro : an international journal published in association with BIBRA · 2020
- Lapachol inhibits the growth of lung cancer by reversing M2-like macrophage polarization via activating NF-κB signaling pathway.Cellular signalling · 2023
- Novel Ru(II)-bipyridine/phenanthroline-lapachol complexes as potential anti-cancer agents.Journal of inorganic biochemistry · 2022
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 242.094294308
Show 5 more facts
- chemical formula
- C₁₅H₁₄O₃
- canonical SMILES
- CC(=CCC1=C(C(=O)c2ccccc2C1=O)O)C
- MCN code
- 2914.69.10
- found in taxon
- Avicennia schaueriana
- Commons category
- Lapachol
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Lapachol is a natural phenolic compound isolated from the bark of the lapacho tree. This tree is known botanically as Handroanthus impetiginosus, but was formerly known by various other botanical names such as Tabebuia avellanedae. Lapachol is also found in other species of Handroanthus.
Lapachol is usually encountered as a yellow, skin-irritating powder from wood. Chemically, it is a derivative of vitamin K.
Excerpted from Wikipedia’s “lapachol” article, available under the CC BY-SA 4.0 licence.