5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylic acid

• ChemBase编号: 132968
• 分子式: C25H22N4O8
• 平均质量: 506.46418
• 单一同位素质量: 506.14376368
• SMILES: Cc1c(c(c(nc1C(=O)O)c1ccc2c(n1)C(=O)C(=C(C2=O)OC)N)N)c1ccc(c(c1O)OC)OC
• Canonical SMILES: COC1=C(N)C(=O)c2c(C1=O)ccc(n2)c1nc(C(=O)O)c(c(c1N)c1ccc(c(c1O)OC)OC)C
• InChI: InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34)
• InChIKey: PVYJZLYGTZKPJE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylic acid
• IUPAC传统名: nigrin
• 别名: Bruneomycin; Nigrin; Streptonigrin from Streptomyces flocculus

登记号

• CAS号: 3930-19-6
• EC号: 223-501-8
• MDL号: MFCD00063401
• Beilstein号: 599390
• PubChem SID: 24899458; 162227245
• PubChem CID: 5351165

理论计算性质

• Acid pKa: 3.8939507
• 质子受体: 12
• 质子供体: 4
• LogD (pH = 5.5): -0.73105085
• LogD (pH = 7.4): -2.248122
• Log P: 1.0583267
• 摩尔折射率: 132.9024 cm^3
• 极化性: 51.534283 Å^3
• 极化表面积: 197.18 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

分子性质

安全信息

• RTECS编号: TJ7350000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 3462
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 1
• 危险公开号: 28
• 安全公开号: 53-28-36/37/39-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300
• GHS警示性声明: P264-P301 + 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 3462 6.1/PG 1
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98%; ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C25H22N4O8

详细说明

Sigma Aldrich - S1014

Biochem/physiol Actions
Streptonigrin (SN) is an aminoquinone antitumour antibiotic. Its antineoplastic activity requires reductive activation by Xanthine-converting enzymes. It induces apoptosis by a mechanism involving NF-κB. DNA cleavage reaction and chromosome damage by SN are influenced by the nature of the metal ion present and dependent on the production of free radicals. Its antibiotic activity is iron-activated.