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

• ChemBase编号: 75733
• 分子式: C11H8O3
• 平均质量: 188.17942
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione
• IUPAC传统名: plumbagin; 5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione
• 别名: 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

登记号

• CAS号: 481-42-5
• EC号: 207-569-6
• MDL号: MFCD00001682
• PubChem SID: 24898833; 162040651
• PubChem CID: 10205
• CHEBI ID: 8273
• CHEMBL: 295316
• Chemspider ID: 9790
• KEGG ID: C10387
• 维基百科标题: Plumbagin

理论计算性质

• Acid pKa: 9.481404
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 2.2362583
• LogD (pH = 7.4): 2.2327461
• Log P: 2.236303
• 摩尔折射率: 52.5212 cm^3
• 极化性: 19.285545 Å^3
• 极化表面积: 54.37 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 75-78°C; 76-78 °C(lit.)

安全信息

• 保存条件: 0°C
• 保存注意事项: Corrosive/Toxic
• RTECS编号: QL8500000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811; 2923
• 德国WGK号: 3
• 联合国危险货物等级: 6.1; 8
• 联合国危险货物包装类别(PG): 2; III
• 澳大利亚Hazchem: 2X
• 危险公开号: 25-34; R:25
• 安全公开号: 22-26-36/37/39-45; S:28-29-36/37/39-45
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• GHS危险品标识: GHS05; GHS06
• GHS警示词: Danger
• GHS危险声明: H301-H314
• GHS警示性声明: P280-P305 + P351 + P338-P310
• 个人保护装置: 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
• 保存温度: -20°C

药理学性质

• 生物活性机理: Suppressor of NF-kB activation, modulator of p65 and 1kB-alpha kinase activation

产品相关信息

• 生物来源: 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
• 应用领域: Exhibits bactericidal; Fungicidal,antimalarial,; tuberculostatic and cardiotonic activity

详细说明

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.

参考文献

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