(2S,4R)-4-({2-[(1R,3R)-1-(acetyloxy)-4-methyl-3-[(2S,3S)-3-methyl-N-{[(3-methylbutanoyl)oxy]methyl}-2-{[(2R)-1-methylpiperidin-2-yl]formamido}pentanamido]pentyl]-1,3-thiazol-4-yl}formamido)-5-(4-hydroxyphenyl)-2-methylpentanoic acid

• ChemBase编号: 153927
• 分子式: C43H65N5O10S
• 平均质量: 844.0687
• 单一同位素质量: 843.44521431
• SMILES: CC[C@H](C)[C@@H](C(=O)N(COC(=O)CC(C)C)[C@H](C[C@H](c1nc(cs1)C(=O)N[C@@H](Cc1ccc(cc1)O)C[C@H](C)C(=O)O)OC(=O)C)C(C)C)NC(=O)[C@H]1CCCCN1C
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N([C@@H](C(C)C)C[C@H](c1scc(n1)C(=O)N[C@H](C[C@@H](C(=O)O)C)Cc1ccc(cc1)O)OC(=O)C)COC(=O)CC(C)C)NC(=O)[C@H]1CCCCN1C)C
• InChI: InChI=1S/C43H65N5O10S/c1-10-27(6)38(46-40(53)34-13-11-12-18-47(34)9)42(54)48(24-57-37(51)19-25(2)3)35(26(4)5)22-36(58-29(8)49)41-45-33(23-59-41)39(52)44-31(20-28(7)43(55)56)21-30-14-16-32(50)17-15-30/h14-17,23,25-28,31,34-36,38,50H,10-13,18-22,24H2,1-9H3,(H,44,52)(H,46,53)(H,55,56)/t27-,28-,31+,34+,35+,36+,38-/m0/s1
• InChIKey: IBEDDHUHZBDXGB-OEJISELMSA-N

名称和登记号

名称

• IUPAC标准名: (2S,4R)-4-({2-[(1R,3R)-1-(acetyloxy)-4-methyl-3-[(2S,3S)-3-methyl-N-{[(3-methylbutanoyl)oxy]methyl}-2-{[(2R)-1-methylpiperidin-2-yl]formamido}pentanamido]pentyl]-1,3-thiazol-4-yl}formamido)-5-(4-hydroxyphenyl)-2-methylpentanoic acid
• IUPAC传统名: (2S,4R)-4-({2-[(1R,3R)-1-(acetyloxy)-4-methyl-3-[(2S,3S)-3-methyl-N-{[(3-methylbutanoyl)oxy]methyl}-2-{[(2R)-1-methylpiperidin-2-yl]formamido}pentanamido]pentyl]-1,3-thiazol-4-yl}formamido)-5-(4-hydroxyphenyl)-2-methylpentanoic acid
• 别名: TubA; Tubulysin A

登记号

• CAS号: 205304-86-5
• MDL号: MFCD12912448
• PubChem SID: 162248066
• PubChem CID: 12134544

理论计算性质

• Acid pKa: 3.6915255
• 质子受体: 10
• 质子供体: 4
• LogD (pH = 5.5): 3.3583734
• LogD (pH = 7.4): 2.9877465
• Log P: 3.3528643
• 摩尔折射率: 221.8516 cm^3
• 极化性: 87.29421 Å^3
• 极化表面积: 204.77 Å^2
• 可自由旋转的化学键: 24
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: organic solvents: soluble
• 外观: colorless or white film

安全信息

• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 23/24/25-36/37/38
• 安全公开号: 36/37-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301-H311-H315-H319-H331-H335
• GHS警示性声明: P261-P280-P301 + P310-P305 + P351 + P338-P311
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95% (HPLC)
• 生物来源: from Streptomyces sp.
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C43H65N5O10S

详细说明

Sigma Aldrich - T3327

Biochem/physiol Actions
Tubulysin A is a novel antibiotic, which is anti-microtubule, anti-mitotic, apoptosis inducer, anticancer, anti-angiogenic, and antiproliferative. Tubulysins are cytotoxic peptides, which include 9 members (A-I). Tubulysin A has potential application as an anticancer agent. It arrests cells in the G2/M phase. Tubulysin A inhibits polymerization more efficiently than vinblastine and induces depolymerization of isolated microtubules. Tubulysin A has potent cytostatic effects on various tumor cell lines with IC50 in the picomolar range.