calcium (3-methyloxiran-2-yl)phosphonate

• ChemBase ID: 133975
• Molecular Formular: C3H5CaO4P
• Molecular Mass: 176.121161
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: calcium (3-methyloxiran-2-yl)phosphonate
• IUPAC Traditional name: calcium (1R,2S)-epoxypropylphosphonate
• Synonyms: calcium (3-methyloxiran-2-yl)phosphonate; (-)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid; Phosphonomycin; Phosphomycin calcium salt; Fosfomycin 钙盐; 磷霉素 钙盐

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 1.2504967
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -3.0407646
• LogD (pH = 7.4): -3.1824315
• Log P: -0.7377749
• Molar Refractivity: 23.6303 cm^3
• Polarizability: 10.472997 Å^3
• Polar Surface Area: 75.72 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Hydrophobicity(logP): -0.425

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%

DETAILS

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).