[2,3-dihydroxy-3-(4H-imidazol-4-yl)propoxy]phosphonic acid

• ChemBase ID: 171547
• Molecular Formular: C6H11N2O6P
• Molecular Mass: 238.135101
• Monoisotopic Mass: 238.03547271
• SMILES: N1=CN=CC1C(C(COP(=O)(O)O)O)O
• Canonical SMILES: OC(C(C1N=CN=C1)O)COP(=O)(O)O
• InChI: InChI=1S/C6H11N2O6P/c9-5(2-14-15(11,12)13)6(10)4-1-7-3-8-4/h1,3-6,9-10H,2H2,(H2,11,12,13)
• InChIKey: SIVIZMCKQNFBMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2,3-dihydroxy-3-(4H-imidazol-4-yl)propoxy]phosphonic acid
• IUPAC Traditional name: 2,3-dihydroxy-3-(4H-imidazol-4-yl)propoxyphosphonic acid
• Synonyms: IGP; D-erythro-Imidazoleglycerol Phosphate Monohydrate

Database IDs

• CAS Number: 210241-69-3
• PubChem SID: 164227457
• PubChem CID: 4150434

CALCULATED PROPERTIES

• Acid pKa: 1.3854415
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -5.072634
• LogD (pH = 7.4): -6.0368986
• Log P: -3.8093646
• Molar Refractivity: 48.081 cm^3
• Polarizability: 19.073156 Å^3
• Polar Surface Area: 131.94 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 127-130°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Storage Warning: Hygroscopic

REFERENCES

• Ames, B.N., et al: J. Gen. Microbiol., 22, 369 (1960)
• Ames, B.N., et al: J. of Biol. Chem., 236, 7, 2019 (1961)