Plumbagin

HCID 10205
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Basic information

CAS
481-42-5
Standard SMILES
CC1=CC(=O)c2c(O)cccc2C1=O
InChIKey
VCMMXZQDRFWYSE-UHFFFAOYSA-N
Molecular formula
C11H8O3
Average molar mass
188.18 g/mol
Monoisotopic mass
188.04734412

Overview

Plumbagin is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively. It has a role as a metabolite, an antineoplastic agent, an anticoagulant and an immunological adjuvant. It is a hydroxy-1,4-naphthoquinone and a member of phenols.

Names & identifiers

Preferred name
Plumbagin
IUPAC
5-hydroxy-2-methylnaphthalene-1,4-dione
English name
PLUMBAGIN
Molecular formula
C11H8O3
Molecular weight
188.18

Names & synonyms

Plumbagin481-42-55-hydroxy-2-methylnaphthalene-1,4-dionePlumbagine5-Hydroxy-2-methyl-1,4-naphthoquinone2-MethyljuglonePlumbaeinPlumbagone5-Hydroxy-2-methyl-1,4-naphthalenedione2-Methyl-5-hydroxy-1,4-naphthoquinone5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dioneNSC-236613
Show more names
plumaginplumbapinPLUMBAGANNSC 236613NSC 688284
YAS4TBQ4OQNSC-688284PCUR-101CHEBI:8273RefChem:863847PCUR101PCUR 101Synthetic Plumbagin PCUR-101

Database identifiers

CAS
481-42-5
PubChem CID
10205
DTXSID
DTXSID8075413
ChEMBL
CHEMBL295316
ChEBI
CHEBI:8273
UNII
YAS4TBQ4OQ
EC Number
207-569-6
Nikkaji
J5.778I

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
54.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
14

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift
Collision Cross Section · 2 items

124.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

134.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
76 · 76-78 °C(lit.)
Boiling point
283.17 °C · 283.17°C (rough estimate)
Density
1.354 · 1.354
refractive index
1.631 · 1.6310 (estimate)
storage temp.
-20 °C · -20°C
solubility
very faint turbidity in hot Methanol

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P264+P265, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 69 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Safety data

wgk
3
rtecs
QL8500000
ridadr
UN 2923 8/PG 2
hs_code
29146990
Toxicity
LD50 i.p. in mice: ~0.015 g/kg (Debray)
risk_code
25-34-36/37/38

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 6 items

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.

Agents that prevent BLOOD CLOTTING.

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).

Chemical substances that prevent or reduce the probability of CONCEPTION.

Applications · 4 items

DescriptionPlumbagin is a natural 1,4-naphthoquinone first isolated from plants of the genus Plumbago. It has diverse effects in cells and animals. Plumbagin causes the generation of reactive oxygen species and induces apoptosis in cancer cells. It activates signaling through Nrf2 and the antioxidant response element, inducing the expression of Nrf2 target genes, including NQO1 and heme oxygenase-1 in cultured neuronal cells. Plumbagin also inhibits NADPH oxidase 4 in a time- and dose-dependent manner. It can be protective against peroxide stress or deprivation of glucose or oxygen.

Usesantibacterial, antifungal, tuberculostatic; antifeedant (worm)

UsesPlumbagin from Plumbago indica has been used: as a reactive oxygen species agent (ROS) to induce cytotoxicity in mouse embryonic fibroblastsas an oxidative stress inducer to generate superoxide anion in Saccharomyces cerevisiaeas a reference standard in thin layer chromatography and in spectrophotometric analysis for quantification of plumbagin in Plumbago auriculate samples

General DescriptionPlumbagin is a bioactive naphthoquinone present majorly in Plumbago indica L. It is a quinoid and is also derived from the roots of Plumbago zeylanicaroots.

Upstream & downstream products

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]

Additional notes

DefinitionChEBI: A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.

Related reactions

1 records
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Compound notes

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