LAPACHOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H14O3
Molecular Weight	242.2699
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)=CCC1=C(O)C(=O)C2=CC=CC=C2C1=O

InChI

InChIKey=CIEYTVIYYGTCCI-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C15H14O3
Molecular Weight	242.2699
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Potency
Plasmodium falciparum 75 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29324340\|https://www.ncbi.nlm.nih.gov/pubmed/21426241	Inhibitor 8504	123.5 µM [IC50]
Oligo-1,6-glucosidase 1 Target ID: CHEMBL5848 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24740357	Inhibitor 8504	11.07 nM [IC50]
Dihydroorotate dehydrogenase 10 Target ID: CHEMBL1966 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10658902	Inhibitor 8504	618.0 nM [IC50]
DNA topoisomerase II alpha 37 Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17713652	Inhibitor 8504
G-protein coupled receptor 35 11 Target ID: CHEMBL1293267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24900447	Agonist 2752	2.84 µM [EC50]

PubMed

Title	Date	PubMed
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.	2011-12-15	21872416
The hydroxy-naphthoquinone lapachol arrests mycobacterial growth and immunomodulates host macrophages.	2010-11	20837170
Quinones as antimycobacterial agents.	2004-09-15	15336259
Inhibitory effects of lapachol derivatives on epstein-barr virus activation.	2003-02-20	12538012
Activity of natural and synthetic naphthoquinones against Toxoplasma gondii, in vitro and in murine models of infection.	2002-09	12375370
Antifungal and antibacterial naphthoquinones from Newbouldia laevis roots.	1996-07	9397206
Comparison of antibacterial and antifungal activities of lapachol and beta-lapachone.	1994-08	7938274
Antiprotozoal quinones. I. Synthesis of 2-hydroxy-3-alkyl-1,4-naphthoquinones as potential coccidiostats.	1968-05	5656473

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:51:46 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:46 GMT 2025`
Record UNII	B221938VB6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-11905

Preferred Name

English

LAPACHOL

Official Name

English

CI 75490

Common Name

English

1,4-NAPHTHALENEDIONE, 2-HYDROXY-3-(3-METHYL-2-BUTENYL)-

Systematic Name

English

C.I. NATURAL YELLOW 16

Common Name

English

GREENHARTIN

Common Name

English

TECOMIN

Common Name

English

C.I. 75490

Common Name

English

NSC-629756

Code

English

LAPACHIC ACID

Common Name

English

2-HYDROXY-3-(3-METHYL-2-BUTEN-1-YL)-1,4-NAPHTHALENEDIONE

Systematic Name

English

LAPACHOL [MI]

Common Name

English

TAIGUIC ACID

Common Name

English

Code System Code Type Description

MERCK INDEX

m6687