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

• ChemBase ID: 154722
• Molecular Formular: C5H11NNaO5P
• Molecular Mass: 219.108071
• Monoisotopic Mass: 219.02725337
• SMILES: CC(=O)N(CCCP(=O)(O)[O-])O.[Na+]
• Canonical SMILES: CC(=O)N(CCCP(=O)(O)[O-])O.[Na+]
• InChI: InChI=1S/C5H12NO5P.Na/c1-5(7)6(8)3-2-4-12(9,10)11;/h8H,2-4H2,1H3,(H2,9,10,11);/q;+1/p-1
• InChIKey: LCFXFDGYDKNWMD-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium hydrogen [3-(N-hydroxyacetamido)propyl]phosphonate
• IUPAC Traditional name: sodium hydrogen 3-(N-hydroxyacetamido)propylphosphonate
• Synonyms: P-[3-(Acetylhydroxyamino)propyl]phosphonic Acid Sodium Salt; [3-(Acetylhydroxyamino)propyl]phosphonic Acid Monosodium Salt; Antibiotic FR 900098 Monosodium Salt; FR 900098 Monosodium Salt; P-[3-(Acetylhydroxyamino)propyl]-phosphonic acid; (3-(Acetylhydroxyamino)propyl)-phosphonic acid; BRN 2096083; FR-900098 monosodium salt

Database IDs

• CAS Number: 73226-73-0
• MDL Number: MFCD17215926
• PubChem SID: 162248860
• PubChem CID: 23665714

CALCULATED PROPERTIES

• Acid pKa: 1.8097414
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -4.4447427
• LogD (pH = 7.4): -4.5530334
• Log P: -2.1551654
• Molar Refractivity: 40.2037 cm^3
• Polarizability: 16.161554 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥20 mg/mL; Methanol; Water
• Apperance: Pale Brown Solid; yellow to orange powder
• Melting Point: 184-186°C

Safety Information

• Storage Condition: desiccated; Hygroscopic, -20°C Freezer, Under Inert Atmosphere; protect from light
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (NMR)
• Empirical Formula (Hill Notation): C5H11NNaO5P

DETAILS

Sigma Aldrich - F8307

Biochem/physiol Actions
1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR) is an enzyme involved in the first step in the nonmevalonate pathway for isoprenoid biosynthesis in Gram-negative, Gram-positive bacteria, plants, and the parasite causing the most virulent form of malaria, Plasmodium falciparum (Mammals produce isoprenoids via the mevalonate pathway). Inhibiton of the enzyme provides alternative to traditional antimalaria therapy. FR-900098 is twice more effective than fosmidomycin against various strains of P. falciparum in vitro and the closely related P. vinckei in mice.

Toronto Research Chemicals - F763500

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)