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

• ChemBase ID: 75733
• Molecular Formular: C11H8O3
• Molecular Mass: 188.17942
• Monoisotopic Mass: 188.04734412
• SMILES: O=C1C(=CC(=O)c2c1cccc2O)C
• Canonical SMILES: CC1=CC(=O)c2c(C1=O)cccc2O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione
• IUPAC Traditional name: plumbagin; 5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione
• Synonyms: Plumbagin from Plumbago indica; 1,4-Dihydro-1,4-dioxo-5-hydroxy-2-methylnaphthalene; 5-Hydroxy-2-methyl-1,4-naphthoquinone; 5-Hydroxy-2-methylnaphthalene-1,4-dione; PLUMBAGIN; Ophioxylin; Plumbagin

Database IDs

• CAS Number: 481-42-5
• EC Number: 207-569-6
• MDL Number: MFCD00001682
• PubChem SID: 24898833; 162040651
• PubChem CID: 10205
• CHEBI ID: 8273
• CHEMBL: 295316
• Chemspider ID: 9790
• KEGG ID: C10387
• Wikipedia Title: Plumbagin

CALCULATED PROPERTIES

• Acid pKa: 9.481404
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.2362583
• LogD (pH = 7.4): 2.2327461
• Log P: 2.236303
• Molar Refractivity: 52.5212 cm^3
• Polarizability: 19.285545 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 75-78°C; 76-78 °C(lit.)

Safety Information

• Storage Condition: 0°C
• Storage Warning: Corrosive/Toxic
• RTECS: QL8500000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811; 2923
• German water hazard class: 3
• Hazard Class: 6.1; 8
• Packing Group: 2; III
• Australian Hazchem: 2X
• Risk Statements: 25-34; R:25
• Safety Statements: 22-26-36/37/39-45; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2923 8/PG 2
• Storage Temperature: -20°C

Pharmacology Properties

• Mechanism of Action: Suppressor of NF-kB activation, modulator of p65 and 1kB-alpha kinase activation

Product Information

• 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
• Application(s): Exhibits bactericidal; Fungicidal,antimalarial,; tuberculostatic and cardiotonic activity

DETAILS

MP Biomedicals - 05217464

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02156282

From Plumbago indica
Orange crystals.

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.

REFERENCES

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