(2S)-2-[(4-{2-[(6R)-2-amino-4-oxo-4H,4aH,5H,6H,7H,8H-pyrido[2,3-d]pyrimidin-6-yl]ethyl}phenyl)formamido]pentanedioic acid

• ChemBase编号: 172375
• 分子式: C21H25N5O6
• 平均质量: 443.4531
• 单一同位素质量: 443.18048355
• SMILES: N1=C(N=C2C(C1=O)C[C@H](CN2)CCc1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O)N
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)CC[C@H]1CNC2=NC(=NC(=O)C2C1)N
• InChI: InChI=1S/C21H25N5O6/c22-21-25-17-14(19(30)26-21)9-12(10-23-17)2-1-11-3-5-13(6-4-11)18(29)24-15(20(31)32)7-8-16(27)28/h3-6,12,14-15H,1-2,7-10H2,(H,24,29)(H,27,28)(H,31,32)(H3,22,23,25,26,30)/t12-,14?,15+/m1/s1
• InChIKey: ZIXNNHANGXIXPX-ATFAPYMMSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-[(4-{2-[(6R)-2-amino-4-oxo-4H,4aH,5H,6H,7H,8H-pyrido[2,3-d]pyrimidin-6-yl]ethyl}phenyl)formamido]pentanedioic acid
• IUPAC传统名: (2S)-2-[(4-{2-[(6R)-2-amino-4-oxo-4aH,5H,6H,7H,8H-pyrido[2,3-d]pyrimidin-6-yl]ethyl}phenyl)formamido]pentanedioic acid
• 别名: N-[4-[2-[(6R)-2-Amino-3,4,5,6,7,8-hexahydro-4-oxopyrido[2,3-d]pyrimidin-6-yl]ethyl]benzoyl]-L-glutamic Acid; LY 264618; Lometrexol

登记号

• CAS号: 106400-81-1
• PubChem SID: 164228285
• PubChem CID: 71749832

理论计算性质

• Acid pKa: 3.0429292
• 质子受体: 10
• 质子供体: 5
• LogD (pH = 5.5): -3.0199182
• LogD (pH = 7.4): -5.7805386
• Log P: -1.5574178
• 摩尔折射率: 111.4643 cm^3
• 极化性: 42.420364 Å^3
• 极化表面积: 183.54 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - L469465

It is an antifolate which inhibits glycinamide ribonucleotide formyltransferase (GARFT), an enzyme essential for de novo purine synthesis. Lometrexol has activity against tumors which are refractory to other drugs, notably Methotrexate.

参考文献

• Gibbs, D., et al.: Cancer Res., 65, 11721 (2005)
• Gangjee, A., et al.: J. Med. Chem., 48, 5329 (2005)
• Hilgenbrink, A., et al.: J. Pharm. Sci., 94, 2135 (2005)