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.

CHEBI:132157 CHEBI:132157
CHEBI:78840 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

Equivalent identifiers for this same structure in other resources.

cas:84-79-7
chemspider:10770962
hmdb:HMDB0253978
kegg.compound:C10366
knapsack:C00002835
wikipedia.en:Lapachol

Activity roles

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

CHEBI:33282 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

Provenance

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