(7R)-7-[(2S)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase编号: 163976
• 分子式: C16H17N3O4S
• 平均质量: 347.38888
• 单一同位素质量: 347.09397704
• SMILES: c1cccc(c1)[C@@H](C(=O)N[C@@H]1C(=O)N2C1SCC(=C2C(=O)O)C)N
• Canonical SMILES: N[C@@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2C1SCC(=C2C(=O)O)C
• InChI: InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11+,15?/m0/s1
• InChIKey: ZAIPMKNFIOOWCQ-FEBOZLGHSA-N

名称和登记号

名称

• IUPAC标准名: (7R)-7-[(2S)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC传统名: (7R)-7-[(2S)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 别名: (6R,7R)-7-[[(2S)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; [6R-[6α,7β(S*)]]-7-[(Aminophenylacetyl)amino]-3-methyl-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-(α-Amino-L-phenylacetamido)-3-deacetoxycephalosporanic Acid; L-Cephalexin

登记号

• CAS号: 34632-04-7
• PubChem SID: 162258111
• PubChem CID: 44318507

理论计算性质

• Acid pKa: 3.4520106
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -2.1413963
• LogD (pH = 7.4): -2.3951817
• Log P: -2.145041
• 摩尔折射率: 88.9736 cm^3
• 极化性: 34.625595 Å^3
• 极化表面积: 112.73 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - C256805

The L-diastereomer of the β-lactam antibiotic Cephalexin (C256800). It is is transported by PEPT1 (the oligopeptide transporter responsible for absorption of peptide nutrients in the small intestine) with high affinity, but is not metabolized by PEPT1 its

参考文献

• Mitsuoka, K. et al.: Biol. Pharmac. Bull., 32, 1459 (2009)
• Snyder, N.J. et al.: Antimicrob. Agents Chemother., 41, 1649 (2009)