CAS 481-42-5|1,4-Dihydro-1,4-dioxo-5-hydroxy-2-methylnaphthalene|5-Hydroxy-2-methylnaphthalene-1,4-dione|plumbagin|5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione|5-Hydroxy-2-methyl-1,4-naphthoq...

General Information

Structure

Molecular Formula

C₁₁H₈O₃

Molecular Mass

188.17942

Exact Mass

188.04734412

Charge

InChI

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

InChIKey

VCMMXZQDRFWYSE-UHFFFAOYSA-N

Canonic Smiles

CC1=CC(=O)c2c(C1=O)cccc2O

Isomeric Smiles

O=C1C(=CC(=O)c2c1cccc2O)C

Calculated Properties

JChem

LogD (pH = 7.4)

2.18

LogD (pH = 5.5)

2.24

Log P

2.24

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

8.28

Polar Surface Area

54.37

Polarizability

18.52

Molar Refractivity

52.52

LOG S

-2.67

Data Source

Names and Identifiers

Synonyms

1,4-Dihydro-1,4-dioxo-5-hydroxy-2-methylnaphthalene5-Hydroxy-2-methylnaphthalene-1,4-dione5-Hydroxy-2-methyl-1,4-naphthoquinonePLUMBAGINPlumbagin from Plumbago indicaOphioxylinPlumbaginPlumbaginplumbaein5-hydroxy-2-methyl-1,4-naphthalenedioneplumbagone5-hydroxy-2-methyl-1,4-naphthoquinoneplumbagineplumbagin2-methyl-5-hydroxy-1,4-naphthoquinone2-methyljuglone

IUPAC Traditional name

plumbagin 5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione

IUPAC name

5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione

Names and Identifiers

Registration numbers

CHEMBL

Chemspider ID

PubChem CID

CHEBI ID

CAS Number

Wikipedia Title

KEGG ID

MDL Number

PubChem SID

1620406512489883311533356

EC Number

207-569-6

EnzymePortal Database

Q9NPH5Q9JHI8Q924V1Q5R5C5

BRENDA Database

1.6.3.11.6.5.21.7.2.54.2.1.93.1.13.21.18.1.21.3.5.12.4.2.303.4.21.731.7.5.11.7.5.21.17.3.42.3.1.482.3.1.321.14.19.631.14.19.682.3.1.471.8.1.121.6.5.51.6.5.10

Patent number

EP1923702US2007238697US2007218124EP1870105

GeneOntology Database

GO:1902709GO:1902708

ACToR Database

481-42-5

UniProt Database

A0QQJ4Q9NPH5P9WKL5A0QUZ4Q9JHI8Q924V1Q5R5C5A0R2W9Q7AKG9

Protein Data Bank

7ca1

SABIO-RK Database

1073811189

MetaboLights Database

MTBLS2207MTBLS2096MTBLS804MTBLS2349MTBLS1693MTBLS2871

Beilstein Number

1870475

PubMed Citation Links

1607870018974148216580272174170716624823215590862106418419748668147625251472791920858709

BRENDA Ligand Database

15431087380132487584563316

Reaxys Registry

1870475

BKMS React Database

13248633161543107584587380

KNApSAcK Database

CompTox Database

LINCS Database

MetaCyc Database

NMRShiftDB Database

SureChEMBL Database

Gmelin ID

PDBeChem Database

BindingDB Database

Registration numbers

Properties

Physical Property

Melting Point

75-78°C

76-78 °C(lit.)

Product Information

Certificate of Analysis

Download link

Application(s)

Exhibits bactericidal

tuberculostatic and cardiotonic activity

Fungicidal,antimalarial,

Biological Source

Constit. of various Plumbago spp., Dyerophyton africanum, Drosera congolana , many Diospyros spp., roots of Dioncophyllum thollonii, Nepenthe rafflesiana, Aristea ecklonii and other Aristea spp., Sisyrinchium californicum and Sparaxis tricolor

Pharmacology Properties

Mechanism of Action

Suppressor of NF-kB activation, modulator of p65 and 1kB-alpha kinase activation

Properties

Related Proteins

PDB Bank

7CA1

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

02156282

From Plumbago indica
Orange crystals.

05217464

MP Biomedicals Rare Chemical collection

Wikipedia

Plumbagin

Sigma Aldrich

P7262

Biochem/physiol Actions
Exhibits cytotoxicity in rodent models of carcinogenesis and carcinoma; has antifungal, antiviral, and antibacterial action.
Plumbagin exhibits cytotoxicity in rodent models of carcinogenesis and carcinoma. Plumbagin is a unique suppressor of CXCR4 expression making in useful in studies of cancer metastasis. Plumbagin has antifungal, antiviral, and antibacterial action.

ChEBI

CHEBI:8273

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.

Molecule Details

References

PubChem Literature

From Data Sources

• Sidhu, G.S. et al., Indian J. Chem., 1968, 6, 681-691, (isol, spectra, deriv)

• Vijayalakshmi, J. et al., Acta Cryst. C, 1987, 43, 2375-2377, (cryst struct)

• Chandrasekaran, B. et al., J. Biosci., 1981, 3, 395-400, (metab)

• Kubo, I. et al., Agric. Biol. Chem., 1983, 47, 911-913, (activity)

• Fieser, L.F. et al., J.A.C.S., 1936, 58, 572-575, (synth)

• Padhye, S.B. et al., J. Phys. Chem., 1975, 79, 927-928, (uv)

• Watanabe, M. et al., Chem. Pharm. Bull., 1986, 34, 2810-2820, (synth)

• Higa, M. et al., Chem. Pharm. Bull., 1998, 46, 1189-1193, (activity, isol)

• Padhye, S.B. et al., J. Magn. Reson., 1974, 16, 150-152, (pmr)

• Takeya, T. et al., Chem. Pharm. Bull., 1999, 47, 209-219, (Me ether, Ac, synth, ir, pmr, cmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PJH610

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 94A, (ir)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 909C, (nmr)

• Ichihara, A. et al., Agric. Biol. Chem., 1980, 44, 211-213, (synth)

• Rama Mohan, H. et al., Indian J. Chem., Sect. B, 1997, 36, 1044-1046, (synth)

• Ghouse, K.M. et al., Z. Kristallogr., Kristallgeom., Kristallphys., Kristallchem., 1974, 139, 335-336, (cryst struct)

• Munday, R. et al., Planta Med., 2000, 66, 399-402, (activity)

• Kubo, I. et al., Planta Med., (Suppl.), 1980, 185-187, (isol)

• Kiuchi, F. et al., Shoyakugaku Zasshi, 1989, 43, 283-293, (activity)

• Durand, R. et al., Tet. Lett., 1971, 3009-3012, (biosynth)

• Wurm, G. et al., Arch. Pharm. (Weinheim, Ger.), 1986, 319, 190-191, (synth)

• Sarkaram, A.V.B. et al., Phytochemistry, 1986, 25, 2867-2871, (cmr)

• Gujar, G.T., Fitoterapia, 1990, 387-394, (rev, pharmacol, props)

• Mohan, P.S. et al., Indian J. Chem., Sect. B, 1997, 36, 1044-1046, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity