lapachol

CHEBI:6377 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:132157
Label unavailable CHEBI:78840

Chemical structure

Computed structure properties
Molecular formula	C15H14O3
Charge	0
Average mass	242.274 Da
Monoisotopic mass	242.09429 Da
Source	ChEBI
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

Also called

2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione (EXACT_SYNONYM)— chebi
2-hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthalenedione (EXACT_SYNONYM)— chebi
2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione (EXACT_SYNONYM)— chebi
2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (EXACT_SYNONYM)— chebi
2-hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione (EXACT_SYNONYM)— chebi
Bethabarra wood (EXACT_SYNONYM)— chebi
C.I. 75490 (EXACT_SYNONYM)— chebi
C.I. natural yellow 16 (EXACT_SYNONYM)— chebi
Ipe-tobacco wood (EXACT_SYNONYM)— chebi
Lapachol (EXACT_SYNONYM)— chebi
Surinam greenheart wood (EXACT_SYNONYM)— chebi
Taigu wood (EXACT_SYNONYM)— chebi
greenhartin (EXACT_SYNONYM)— chebi
lapachol wood (EXACT_SYNONYM)— chebi
taiguic acid (EXACT_SYNONYM)— chebi
tecomin (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Lapachol

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antibacterial agent CHEBI:33282

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:6377`	lapachol	`antibioticmech:chebi-63264ba58d`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

Explore across X-Mech: MediaIngredientMech (lapachol) · CultureMech · NaturalProductMech · PathwayMech · TraitMech