{[(2R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 160672
• Molecular Formular: C6H13O8P
• Molecular Mass: 244.136381
• Monoisotopic Mass: 244.03480401
• SMILES: [C@@H]1(C([C@H](O[C@H]1CO)COP(=O)(O)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](C([C@@H]1O)O)COP(=O)(O)O
• InChI: InChI=1S/C6H13O8P/c7-1-3-5(8)6(9)4(14-3)2-13-15(10,11)12/h3-9H,1-2H2,(H2,10,11,12)/t3-,4+,5-,6?/m0/s1
• InChIKey: XYTKBMAMGDBXPU-AMVSKUEXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxyphosphonic acid
• Synonyms: 2,5-Anhydro-D-glucitol 6-(Dihydrogen Phosphate); 2,5-Anhydro-D-glucitol-6-phosphate

Database IDs

• CAS Number: 73548-76-2
• PubChem SID: 162254807
• PubChem CID: 71313420

CALCULATED PROPERTIES

• Acid pKa: 1.2300867
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -5.132665
• LogD (pH = 7.4): -6.2176905
• Log P: -2.6918814
• Molar Refractivity: 45.7664 cm^3
• Polarizability: 19.052965 Å^3
• Polar Surface Area: 136.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Brown Viscous Oil

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A648040

An effective competitive inhibitor of phosphofructokinase (EC 2.7.1.11).

REFERENCES

• Koerner Jr., T.A.W. et al.: JBC 249(18)
• 5749-5754 (18)
• Reitz, A.B. et al.: Tetrahedron Letters, 26(18)
• 3915-3918 (1985)