(2S)-2-[(5-{methyl[(2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid hydrate

• ChemBase编号: 154385
• 分子式: C21H24N4O7S
• 平均质量: 476.50286
• 单一同位素质量: 476.13657013
• SMILES: Cc1[nH]c(=O)c2cc(ccc2n1)CN(C)c1ccc(s1)C(=O)N[C@@H](CCC(=O)O)C(=O)O.O
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(s1)N(Cc1ccc2c(c1)c(=O)[nH]c(n2)C)C.O
• InChI: InChI=1S/C21H22N4O6S.H2O/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27;/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28);1H2/t15-;/m0./s1
• InChIKey: VADKIFZZQGWGDT-RSAXXLAASA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-[(5-{methyl[(2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid hydrate
• IUPAC传统名: (2S)-2-[(5-{methyl[(2-methyl-4-oxo-3H-quinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid hydrate
• 别名: L-Glutamic acid, N-((5-(((1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thienyl)carbonyl)- monohydrate; ICI-D-1694; ZD-1694; Raltitrexed monohydrate

登记号

• MDL号: MFCD12828867
• PubChem SID: 162248524
• PubChem CID: 14256589

理论计算性质

• Acid pKa: 3.9605484
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): -1.3607305
• LogD (pH = 7.4): -4.7035975
• Log P: 0.7630046
• 摩尔折射率: 117.8249 cm^3
• 极化性: 43.176983 Å^3
• 极化表面积: 148.4 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: ≥40 mg/mL; H2O: ≥10 mg/mL
• 外观: off-white to light yellow solid

安全信息

• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 2
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 61-25
• 安全公开号: 53-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H300-H360
• GHS警示性声明: P201-P264-P301 + P310-P308 + P313
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H22N4O6S · H2O

详细说明

Sigma Aldrich - R9156

Biochem/physiol Actions
Raltitrexed is a folate-based inhibitor of thymidylate synthase (TS) that is rapidly and extensively metabolized to its more potent polyglutamate derivatives. By inhibiting the formation of precursor pyrimidine nucleotides, raltitrexed prevents the formation of DNA and RNA, which are required for the growth and survival of both normal cells and cancer cells.