sodium (6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase编号: 155518
• 分子式: C15H16N7NaO5S3
• 平均质量: 493.51621
• 单一同位素质量: 493.02727393
• SMILES: Cn1c(nnn1)SCC1=C(N2[C@@H]([C@@](C2=O)(NC(=O)CSCC#N)OC)SC1)C(=O)[O-].[Na+]
• Canonical SMILES: N#CCSCC(=O)N[C@]1(OC)C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])CSc1nnnn1C.[Na+]
• InChI: InChI=1S/C15H17N7O5S3.Na/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25;/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25);/q;+1/p-1/t13-,15+;/m1./s1
• InChIKey: BITQGIOJQWZUPL-PBCQUBLHSA-M

名称和登记号

名称

• IUPAC标准名: sodium (6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC传统名: sodium cefmetazole(1-)
• 别名: Cefmetazole sodium salt

登记号

• CAS号: 56796-39-5
• MDL号: MFCD00214260
• PubChem SID: 162249656; 24278328
• PubChem CID: 23666711

理论计算性质

• Acid pKa: 3.3825634
• 质子受体: 9
• 质子供体: 1
• LogD (pH = 5.5): -2.7527611
• LogD (pH = 7.4): -4.0735326
• Log P: -0.6482912
• 摩尔折射率: 135.4078 cm^3
• 极化性: 42.302906 Å^3
• 极化表面积: 166.16 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

分子性质

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 2
• 危险公开号: 36/37/38-42/43
• 安全公开号: 26-36
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H315-H317-H319-H334-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338-P342 + P311
• 保存温度: 2-8°C

产品相关信息

• 有效期: (limited shelf life, expiry date on the label)
• 线性分子式: C15H16N7O5S3Na

详细说明

Sigma Aldrich - C6048

Application
Cefmetazole is used to study the effect of expression, binding, and inhibition of penicillin-binding proteins (PDPs) other than PBP2 on bacterial cell wall mucopeptide synthesis. Cefmetazole is used to study protein mediated transport of antibiotics .
Cefmetazole is used to study the effect of expression, binding, and inhibition of penicillin-binding proteins (PDPs) other than PBP2 on bacterial cell wall mucopeptide synthesis.
Biochem/physiol Actions
Cefmetazole disrupts the synthesis of the peptidoglycan layer of bacterial cell walls which is responsible for cell wall structural integrity. Peptidoglycan synthesis is facilitated by transpeptidases known as penicillin-binding proteins (PBPs). PBPs bind to the D-Ala-D-Ala at the end of muropeptides (peptidoglycan precursors) to crosslink the peptidoglycan. Cefmetazole mimics the D-Ala-D-Ala site, thereby competitively inhibiting PBP crosslinking of peptidoglycan.