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=C(C=CC=C2)C1=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 74 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29324340\|https://www.ncbi.nlm.nih.gov/pubmed/21426241	Inhibitor 8297	123.5 µM [IC50]
Oligo-1,6-glucosidase 1 Target ID: CHEMBL5848 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24740357	Inhibitor 8297	11.07 nM [IC50]
Dihydroorotate dehydrogenase 9 Target ID: CHEMBL1966 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10658902	Inhibitor 8297	618.0 nM [IC50]
DNA topoisomerase II alpha 37 Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17713652	Inhibitor 8297
G-protein coupled receptor 35 11 Target ID: CHEMBL1293267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24900447	Agonist 2678	2.84 µM [EC50]

PubMed

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

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:15:19 UTC 2023` Edited by `admin` on `Fri Dec 15 15:15:19 UTC 2023`
Record UNII	B221938VB6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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-11905

Code

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