5,21-dichloro-23-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1(16),2(10),4,6,8,11(15),17(22),18,20-nonaene-12,14-dione

• ChemBase编号: 155075
• 分子式: C27H21Cl2N3O7
• 平均质量: 570.37754
• 单一同位素质量: 569.07565539
• SMILES: CO[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)n1c2c(cccc2Cl)c2c1c1c(c3cccc(c3[nH]1)Cl)c1c2c(=O)[nH]c1=O)CO
• Canonical SMILES: CO[C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)n1c2c(Cl)cccc2c2c1c1[nH]c3c(c1c1c2c(=O)[nH]c1=O)cccc3Cl
• InChI: InChI=1S/C27H21Cl2N3O7/c1-38-24-13(8-33)39-27(23(35)22(24)34)32-20-10(5-3-7-12(20)29)15-17-16(25(36)31-26(17)37)14-9-4-2-6-11(28)18(9)30-19(14)21(15)32/h2-7,13,22-24,27,30,33-35H,8H2,1H3,(H,31,36,37)/t13-,22-,23-,24-,27-/m1/s1
• InChIKey: QEHOIJJIZXRMAN-QZQSLCQPSA-N

名称和登记号

名称

• IUPAC标准名: 5,21-dichloro-23-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0^2,^1^0.0^4,^9.0^1^1,^1^5.0^1^7,^2^2]tricosa-1(16),2(10),4,6,8,11(15),17(22),18,20-nonaene-12,14-dione
• IUPAC传统名: rebeccamycin
• 别名: Rebeccamycin

登记号

• CAS号: 93908-02-2
• MDL号: MFCD01718312
• PubChem SID: 162249213; 24899375
• PubChem CID: 73110

理论计算性质

• Acid pKa: 8.051588
• 质子受体: 7
• 质子供体: 5
• LogD (pH = 5.5): 2.5884032
• LogD (pH = 7.4): 2.5032644
• Log P: 2.5896325
• 摩尔折射率: 141.0628 cm^3
• 极化性: 58.73478 Å^3
• 极化表面积: 146.04 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: ≥3 mg/mL; THF: soluble
• 外观: yellow solid

安全信息

• 保存条件: protect from light
• 德国WGK号: -
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... TOP1(7150)mouse ... Prkca(18750)rat ... Prkca(24680)

产品相关信息

• 纯度: ≥98% (HPLC)
• 生物来源: from Saccharothrix aerocolonigenes
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C27H21Cl2N3O7

详细说明

Sigma Aldrich - R4900

Biochem/physiol Actions
Rebeccamycin is an antibiotic composed of a halogenated indolocarbazole chromophore linked via N-glycosidic bond to a glucose derivative. As an antitumor agent,1 it is cytotoxic to tumor cell lines such as human lung adenocarcinoma, colon carcinoma and nasopharyngeal carcinoma, etc.2 Rebeccamycin intercalates into the DNA and is an inhibitor of topoisomerase I. It stabilizes the covalent topoisomerase I-DNA intermediate (the cleavable complex) resulting in increased DNA strand breaks.3