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

• ChemBase ID: 160671
• Molecular Formular: C6H14O11P2
• Molecular Mass: 324.116282
• Monoisotopic Mass: 324.00113453
• SMILES: [C@@H]1(C([C@H](O[C@H]1COP(=O)(O)O)COP(=O)(O)O)O)O
• Canonical SMILES: OC1[C@@H](COP(=O)(O)O)O[C@H]([C@H]1O)COP(=O)(O)O
• InChI: InChI=1S/C6H14O11P2/c7-5-3(1-15-18(9,10)11)17-4(6(5)8)2-16-19(12,13)14/h3-8H,1-2H2,(H2,9,10,11)(H2,12,13,14)/t3-,4+,5-,6?/m0/s1
• InChIKey: WSMBXSQDFPTODV-AMVSKUEXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,4R,5S)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,4R,5S)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid
• Synonyms: 2,5-anhydro-D-glucitol 1,6-Bis(dihydrogen phosphate); 2,5-Anhydroglucitol 1,6-Bisphosphate; 2,5-Anhydro-D-glucitol-1,6-diphosphate

Database IDs

• CAS Number: 4429-47-4
• PubChem SID: 162254806
• PubChem CID: 71313419

CALCULATED PROPERTIES

• Acid pKa: 0.92905384
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -7.697015
• LogD (pH = 7.4): -9.867063
• Log P: -2.8154473
• Molar Refractivity: 56.6393 cm^3
• Polarizability: 23.718092 Å^3
• Polar Surface Area: 183.21 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Yellow Gel

Safety Information

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

DETAILS

Toronto Research Chemicals - A648020

An effective competitive inhibitor of phosphofructokinase (EC 2.7.1.11).

REFERENCES

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