(2S)-1-[(2S)-2-benzyl-3-methoxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]-3-methyl-1-oxobutan-2-yl (2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-(dimethylamino)-3-methylbutanamido]-N,3-dimethylbutanamido]-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate

• ChemBase编号: 153752
• 分子式: C45H68N6O9
• 平均质量: 837.05622
• 单一同位素质量: 836.50477779
• SMILES: CC(C)[C@@H](C(=O)N(C)[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)O[C@@H](C(C)C)C(=O)N1[C@H](C(=CC1=O)OC)Cc1ccccc1)NC(=O)[C@H](C(C)C)N(C)C
• Canonical SMILES: COC1=CC(=O)N([C@H]1Cc1ccccc1)C(=O)[C@H](C(C)C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@@H](N(C(=O)[C@H](C(C)C)NC(=O)[C@@H](N(C)C)C(C)C)C)C(C)C
• InChI: InChI=1S/C45H68N6O9/c1-26(2)36(46-40(53)37(27(3)4)47(9)10)42(55)48(11)38(28(5)6)43(56)49-22-16-20-31(49)41(54)50-23-17-21-32(50)45(58)60-39(29(7)8)44(57)51-33(34(59-12)25-35(51)52)24-30-18-14-13-15-19-30/h13-15,18-19,25-29,31-33,36-39H,16-17,20-24H2,1-12H3,(H,46,53)/t31-,32-,33-,36-,37-,38-,39-/m0/s1
• InChIKey: LQKSHSFQQRCAFW-CCVNJFHASA-N

名称和登记号

名称

• IUPAC标准名: (2S)-1-[(2S)-2-benzyl-3-methoxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]-3-methyl-1-oxobutan-2-yl (2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-(dimethylamino)-3-methylbutanamido]-N,3-dimethylbutanamido]-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate
• IUPAC传统名: (2S)-1-[(2S)-2-benzyl-3-methoxy-5-oxo-2H-pyrrol-1-yl]-3-methyl-1-oxobutan-2-yl (2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-(dimethylamino)-3-methylbutanamido]-N,3-dimethylbutanamido]-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate
• 别名: (5S)-1-[(2S)-O-(N,N-Val-Val-N-Me-Val-Pro-Pro)-2-hydroxyisovaleryl]-2-oxo-4-methoxy-5-benzyl-3-pyrroline; Dolastatin 15

登记号

• CAS号: 123884-00-4
• MDL号: MFCD00236968
• PubChem SID: 162247891; 24893943
• PubChem CID: 9918978

理论计算性质

• Acid pKa: 9.828692
• 质子受体: 9
• 质子供体: 1
• LogD (pH = 5.5): 1.4148394
• LogD (pH = 7.4): 3.1796803
• Log P: 3.7981162
• 摩尔折射率: 227.1618 cm^3
• 极化性: 88.88065 Å^3
• 极化表面积: 166.18 Å^2
• 可自由旋转的化学键: 18
• 里宾斯基五规则: false

分子性质

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ≥95%
• Empirical Formula (Hill Notation): C45H68N6O9

详细说明

Sigma Aldrich - D5566

Amino Acid Sequence
Val-Val-NMe-Val-Pro-Pro-2-hydroxyisovaleryl-2-oxo-4-methoxy-5-benzyl-3-pyrroline
Application
An anti-neoplastic pseudopeptide originally isolated from the sea hare Dolabella auricularia. Reported to interact with tubulin and induce apoptosis. Potent inhibitor of the proliferation of murine and cancer cell lines as well as of hematopoietic progenitor cells.