PLUMBAGIN

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H8O3
Molecular Weight	188.1794
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(=O)C2=C(O)C=CC=C2C1=O

InChI

InChIKey=VCMMXZQDRFWYSE-UHFFFAOYSA-N

InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3

HIDE SMILES / InChI

Molecular Formula	C11H8O3
Molecular Weight	188.1794
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
Pancreatic lipase 5 Target ID: CHEMBL1812 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29672969	Inhibitor 8504	82.08 µM [IC50]
Cytochrome P450 2J2 4 Target ID: CHEMBL3491 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29433675	Inhibitor 8504	3.82 µM [IC50]
Hepatitis C virus 23 Target ID: CHEMBL379 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27215409	Inhibitor 8504	0.57 µM [IC50]
Cytochrome P450 1A2 73 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26614990	Inhibitor 8504	1.39 µM [IC50]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26614990	Inhibitor 8504	2.37 µM [IC50]
Histone acetyltransferase p300 7 Target ID: CHEMBL3784 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26701186	Inhibitor 8504	2.0 µM [IC50]
Plasmodium falciparum 75 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19299148	Inhibitor 8504	270.0 nM [IC50]
Trypanothione reductase 5 Target ID: CHEMBL5131 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11170645\|https://www.ncbi.nlm.nih.gov/pubmed/10762041	Inhibitor 8504	28.0 µM [IC50]

PubMed

Title	Date	PubMed
The development of a reagentless lactate biosensor based on a novel conducting polymer.	2006-05	16263338
Transformation of carbon tetrachloride by bisulfide treated goethite, hematite, magnetite, and kaolinite.	2006-04	16154172
The whcE gene of Corynebacterium glutamicum is important for survival following heat and oxidative stress.	2005-11-25	16212936
Investigation into the resistance of lactoperoxidase tolerant Escherichia coli mutants to different forms of oxidative stress.	2005-11-15	16209909
High-performance liquid chromatography for quantification of plumbagin, an anti-Helicobacter pylori compound of Plumbago zeylanica L.	2005-11-11	16257295
Transformation of carbon tetrachloride by thiol reductants in the presence of quinone compounds.	2005-10-01	16245816
Candida albicans-conditioned medium protects yeast cells from oxidative stress: a possible link between quorum sensing and oxidative stress resistance.	2005-10	16215173
Soy isoflavone glycitein protects against beta amyloid-induced toxicity and oxidative stress in transgenic Caenorhabditis elegans.	2005-08-25	16122394
Determination and identification of plumbagin from the roots of Plumbago zeylanica L. by liquid chromatography with tandem mass spectrometry.	2005-08-12	16078700
Phenolic acids, syringaldehyde, and juglone in fruits of different cultivars of Juglans regia L.	2005-08-10	16076123
Induction of phenotypes resembling CuZn-superoxide dismutase deletion in wild-type yeast cells: an in vivo assay for the role of superoxide in the toxicity of redox-cycling compounds.	2005-08	16097801
Isolation of secondary metabolites from roots of Plumbago auriculata Lam. by countercurrent chromatography.	2005-07-27	16042155
Secondary metabolites in in vitro cultured plants of the genus Drosera.	2005-07-07	15997845
Effect of quinones on microtubule polymerization: a link between oxidative stress and cytoskeletal alterations in Alzheimer's disease.	2005-06-10	15949717
[Collection of Arabidopsis thaliana mutants with altered sensitivity to oxidative stress inductors].	2005-06-02	15926316
Bacillus subtilis paraquat resistance is directed by sigmaM, an extracytoplasmic function sigma factor, and is conferred by YqjL and BcrC.	2005-05	15838020
Feeding response to host and nonhost compounds by males and females of the spruce bark beetle Ips typographus in a tunneling microassay.	2005-04	16124249
Unique stress response to the lactoperoxidase-thiocyanate enzyme system in Escherichia coli.	2005-03	15748988
Selective growth-inhibiting effects of compounds identified in Tabebuia impetiginosa inner bark on human intestinal bacteria.	2005-02-23	15713033
Phosphorylation modulates the alpha-helical structure and polymerization of a peptide from the third tau microtubule-binding repeat.	2005-01-18	15652175
Reversal of a full-length mutant huntingtin neuronal cell phenotype by chemical inhibitors of polyglutamine-mediated aggregation.	2005-01-13	15649316
Peroxiredoxin-linked detoxification of hydroperoxides in Toxoplasma gondii.	2005-01-07	15507457
Inhibition of Nox-4 activity by plumbagin, a plant-derived bioactive naphthoquinone.	2005-01	15638999
An extract from teak (Tectona grandis) bark inhibited Listeria monocytogenes and methicillin resistant Staphylococcus aureus.	2005	15960759
A fluorescence-based rapid screening assay for cytotoxic compounds.	2004-12-24	15555600
Separation methods of quinonoid constituents of plants used in Oriental traditional medicines.	2004-12-05	15556503
Photoreactions of 1,4-Naphthoquinones: effects of substituents and water on the intermediates and reactivity.	2004-11-25	15560739
Antimicrobial activity and chemical investigation of Brazilian Drosera.	2004-11	15654434
Antimycobacterial constituents from Juniperus procera, Ferula communis and Plumbago zeylanica and their in vitro synergistic activity with isonicotinic acid hydrazide.	2004-11	15597311
NO reductase from Bacillus azotoformans is a bifunctional enzyme accepting electrons from menaquinol and a specific endogenous membrane-bound cytochrome c551.	2004-10-26	15491156
Co-induction of methyltransferase Rv0560c by naphthoquinones and fibric acids suggests attenuation of isoprenoid quinone action in Mycobacterium tuberculosis.	2004-10	15644891
Quinones as antimycobacterial agents.	2004-09-15	15336259
Plumbagin quantification in roots of Plumbago scandens L. obtained by different extraction techniques.	2004-09	15334248
Proteome-level differences between auxinic-herbicide-susceptible and -resistant wild mustard (Sinapis arvensis L.).	2004-08-11	15291476
Oxy2 as a transcriptional activator gene for copper uptake in Cryptococcus neoformans.	2004-08	15473357
Degradation of juglone by Pleurotus sajor-caju.	2004-08	15449596
Plumbagin induces reactive oxygen species, which mediate apoptosis in human cervical cancer cells.	2004-08	15264212
Superoxide dismutase mimetics elevate superoxide dismutase activity in vivo but do not retard aging in the nematode Caenorhabditis elegans.	2004-07-15	15203195
Isolation of long-lived mutants in Caenorhabditis elegans using selection for resistance to juglone.	2004-07-15	15203185
Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia.	2004-07	15270571
Cytotoxic constituents from Plumbago zeylanica.	2004-07	15261389
Multisite phosphorylation of Pin1-associated mitotic phosphoproteins revealed by monoclonal antibodies MPM-2 and CC-3.	2004-06-01	15171797
Antitermitic quinones from Diospyros sylvatica.	2004-05	15184011
Juglone disrupts root plasma membrane H+-ATPase activity and impairs water uptake, root respiration, and growth in soybean (Glycine max) and corn (Zea mays).	2004-02	15112735
Role of NAD(P)H:quinone oxidoreductase encoded by drgA gene in reduction of exogenous quinones in cyanobacterium Synechocystis sp. PCC 6803 cells.	2004-02	15000679
Direct oxidation of 2',7'-dichlorodihydrofluorescein by pyocyanin and other redox-active compounds independent of reactive oxygen species production.	2004-01-01	14732293
Antioxidant properties of Plumbago zeylanica, an Indian medicinal plant and its active ingredient, plumbagin.	2004	15479566
Source of tryptone in growth medium affects oxidative stress resistance in Escherichia coli.	2004	15186449
Antimicrobial activity in vitro of plumbagin isolated from Plumbago species.	2003-10	14762525
Medicinal herb extract and a single-compound drug confer similar complex pharmacogenomic activities in mcf-7 cells.	2003-06-30	15067226

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:17:40 GMT 2025` Edited by `admin` on `Mon Mar 31 19:17:40 GMT 2025`
Record UNII	YAS4TBQ4OQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-236613

Preferred Name

English

PLUMBAGIN

Common Name

English

PLUMBAGIN [MI]

Common Name

English

NSC-688284

Code

English

PCUR-101

Code

English

Plumbagin [WHO-DD]

Common Name

English

5-HYDROXY-2-METHYL-1,4-NAPHTHALENEDIONE

Systematic Name

English

Code System Code Type Description

NSC

688284