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

• ChemBase编号: 154722
• 分子式: C5H11NNaO5P
• 平均质量: 219.108071
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: sodium hydrogen [3-(N-hydroxyacetamido)propyl]phosphonate
• IUPAC传统名: sodium hydrogen 3-(N-hydroxyacetamido)propylphosphonate
• 别名: 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

登记号

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

理论计算性质

• Acid pKa: 1.8097414
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): -4.4447427
• LogD (pH = 7.4): -4.5530334
• Log P: -2.1551654
• 摩尔折射率: 40.2037 cm^3
• 极化性: 16.161554 Å^3
• 极化表面积: 100.9 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: H2O: ≥20 mg/mL; Methanol; Water
• 外观: Pale Brown Solid; yellow to orange powder
• 熔点: 184-186°C

安全信息

• 保存条件: desiccated; Hygroscopic, -20°C Freezer, Under Inert Atmosphere; protect from light
• 德国WGK号: 3
• 保存温度: -20°C

产品相关信息

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

详细说明

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.

参考文献

• 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)