(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-(oxan-2-yloxy)oxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase编号: 72657
• 分子式: C32H37NO12
• 平均质量: 627.63568
• 单一同位素质量: 627.23157563
• SMILES: [C@@H]1([C@H]([C@H](C[C@@H](O1)O[C@@H]1c2c(C[C@](C1)(C(=O)CO)O)c(c1c(c2O)C(=O)c2c(C1=O)cccc2OC)O)N)OC1OCCCC1)C
• Canonical SMILES: OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@@H]([C@@H](O2)C)OC2CCCCO2)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
• InChI: InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21?,22-,31+,32-/m0/s1
• InChIKey: KMSKQZKKOZQFFG-NCXNULAVSA-N

名称和登记号

名称

• IUPAC标准名: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-(oxan-2-yloxy)oxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC传统名: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-(oxan-2-yloxy)oxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
• 别名: THP; Pirarubicin; THP-Adriamycin; Pirarubicin

登记号

• CAS号: 72496-41-4
• MDL号: MFCD00869742
• PubChem SID: 162037582
• PubChem CID: 6917695

理论计算性质

• Acid pKa: 9.478123
• 质子受体: 13
• 质子供体: 5
• LogD (pH = 5.5): 0.1203337
• LogD (pH = 7.4): 1.3603758
• Log P: 2.5154042
• 摩尔折射率: 157.3784 cm^3
• 极化性: 61.92432 Å^3
• 极化表面积: 204.3 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: false

分子性质

安全信息

• 保存条件: -20°C
• 德国WGK号: 3
• 保存温度: 2-8°C

药理学性质

• 作用靶点: topoisomerase

产品相关信息

• 纯度: ≥95% (HPLC)
• 成盐信息: Free Base
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C32H37NO12

详细说明

Selleck Chemicals - S1393

Research Area: Cancer
Biological Activity:
Pirarubicin is an anthracycline drug. An analogue of the anthracycline antineoplastic antibiotic doxorubicin. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines. [1,2]References on Pirarubicin[1] http://www.cancer.gov/drugdictionary/?CdrID=38775, , [2] http://en.wikipedia.org/wiki/Pirarubicin, ,

Sigma Aldrich - P8624

Biochem/physiol Actions
Anthracycline antibiotic that is an analog of doxorubicin. Antineoplastic. Pirarubicin is transported into cells vial a sodium-dependent nucleoside transporter.1,2 It is used to intercalate DNA and inhibit the activity of topoisomerase II and induce DNA crosslinking.
Application
Pirarubicin, an anthracycline antibiotic, is an anticancer drug. Pirarubicin is used to study synergistic cytotoxicity and apoptosis of cancer cells1,2. It is used to study how to protect multi-drug resistance cells from anthracycline induced cytotoxicity3.

参考文献

• http://en.wikipedia.org/wiki/Pirarubicin