calcium (3-methyloxiran-2-yl)phosphonate

• ChemBase编号: 133975
• 分子式: C3H5CaO4P
• 平均质量: 176.121161
• 单一同位素质量: 175.95513625
• SMILES: CC1C(O1)P(=O)([O-])[O-].[Ca+2]
• Canonical SMILES: CC1OC1P(=O)([O-])[O-].[Ca+2]
• InChI: InChI=1S/C3H7O4P.Ca/c1-2-3(7-2)8(4,5)6;/h2-3H,1H3,(H2,4,5,6);/q;+2/p-2
• InChIKey: YMZJBJPWTXJQMR-UHFFFAOYSA-L

名称和登记号

名称

• IUPAC标准名: calcium (3-methyloxiran-2-yl)phosphonate
• IUPAC传统名: calcium (1R,2S)-epoxypropylphosphonate
• 别名: Fosfomycin 钙盐; 磷霉素 钙盐; calcium (3-methyloxiran-2-yl)phosphonate; (-)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid; Phosphonomycin; Phosphomycin calcium salt

登记号

• CAS号: 26016-98-8
• EC号: 247-408-7
• MDL号: MFCD07809417; MFCD00070095
• PubChem SID: 162228252; 24898888
• PubChem CID: 5702189

理论计算性质

• Acid pKa: 1.2504967
• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): -3.0407646
• LogD (pH = 7.4): -3.1824315
• Log P: -0.7377749
• 摩尔折射率: 23.6303 cm^3
• 极化性: 10.472997 Å^3
• 极化表面积: 75.72 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 疏水性(logP): -0.425

安全信息

• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: 95%

详细说明

Sigma Aldrich - P7902

Application
Phosphomycin, also known as Fosfomycin, is an antibiotic produced by Streptomyces fradiae. It is used to treat uncomplicated urinary tract infections and to reduce nephrotoxicity and ototoxicity of platinum-containing anti-tumor agents. It is used to study resistance proteins in Bacillus subtilis1 and Mycobacterium tuberculosis2. It is a potential treatment for bronchiectasis3.
Biochem/physiol Actions
Fosfomycin is a phosphoenolpyruvate analog. It irreversibly inhibits enolpyruvate transferase (MurA). Therefore, the producion of N-acetylmuramic acid, an essential element of the peptidoglycan cell wall is inhibited.
Phosphomycin calcium salt blocks the formation or N-acetylmuramic acid by inhibiting UDP-Nacetylglucosamine 3-enolpyruvate transferase (MurA).