sodium hydrogen [3-(N-hydroxyformamido)propyl]phosphonate

• ChemBase ID: 169453
• Molecular Formular: C4H9NNaO5P
• Molecular Mass: 205.081491
• Monoisotopic Mass: 205.0116033
• SMILES: N(CCCP(=O)(O)[O-])(O)C=O.[Na+]
• Canonical SMILES: O=CN(CCCP(=O)(O)[O-])O.[Na+]
• InChI: InChI=1S/C4H10NO5P.Na/c6-4-5(7)2-1-3-11(8,9)10;/h4,7H,1-3H2,(H2,8,9,10);/q;+1/p-1
• InChIKey: ZZPUYRHMTGOTEU-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium hydrogen [3-(N-hydroxyformamido)propyl]phosphonate
• IUPAC Traditional name: sodium hydrogen 3-(N-hydroxyformamido)propylphosphonate
• Synonyms: 3-(N-Formyl-N-hydroxyamino)propyl Phosphonic Acid Sodium Salt; FR31564; Fosmidomycin Sodium Salt

Database IDs

• CAS Number: 66508-37-0
• PubChem SID: 162263585
• PubChem CID: 5141362

CALCULATED PROPERTIES

• Acid pKa: 1.8097415
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -4.5007024
• LogD (pH = 7.4): -4.6011925
• Log P: -2.2112334
• Molar Refractivity: 35.7132 cm^3
• Polarizability: 14.376273 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 189-191°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F728500

The antibiotics Fosmidomycin and FR900098 are members of a unique class of phosphonic acid natural products that inhibit the nonmevalonate pathway for isoprenoid biosynthesis. Both are potent antibacterial and antimalarial compounds.

REFERENCES

• Altschul, S., et al.: J. Mol. Biol., 215, 403 (1990)
• Altschul, S., et al.: J. Mol. Biol., 215, 403 (1990)
• Noda, M., et al.: J. Biol. Chem., 279, 46143 (1990)
• Snow, R., et al.: Nature, 434, 214 (1990)