(2R,3R)-2,3-dihydroxy-4-(phosphonooxy)butanoic acid

• ChemBase ID: 176686
• Molecular Formular: C4H9O8P
• Molecular Mass: 216.083221
• Monoisotopic Mass: 216.00350388
• SMILES: C([C@H]([C@@H](O)C(=O)O)O)OP(=O)(O)O
• Canonical SMILES: O[C@@H]([C@H](C(=O)O)O)COP(=O)(O)O
• InChI: InChI=1S/C4H9O8P/c5-2(3(6)4(7)8)1-12-13(9,10)11/h2-3,5-6H,1H2,(H,7,8)(H2,9,10,11)/t2-,3-/m1/s1
• InChIKey: ZCZXOHUILRHRQJ-PWNYCUMCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxy-4-(phosphonooxy)butanoic acid
• IUPAC Traditional name: 4-phospho-D-erythronic acid
• Synonyms: (2R,3R)-2,3-Dihydroxy-4-(phosphonooxy)butanoic Acid; [R-(R*,R*)]-2,3-Dihydroxy-4-(phosphonooxy)butanoic Acid; 4-Phospho D-Erythronate

Database IDs

• CAS Number: 57229-25-1
• PubChem SID: 164232596
• PubChem CID: 449304

CALCULATED PROPERTIES

• Acid pKa: 1.466217
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -6.6976047
• LogD (pH = 7.4): -8.872041
• Log P: -2.2726405
• Molar Refractivity: 37.2189 cm^3
• Polarizability: 15.463317 Å^3
• Polar Surface Area: 144.52 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P355000

4-Phospho-D-erythronate is an intermediate in the synthesis of pyridoxal 5'-phosphate in some bacteria and an inhibitor of ribose 5-phosphate isomerase. Phosphorylated aldonic acids are strong inhibitors of 6-phosphogluconate dehydrogenase, and 4-phospho-

REFERENCES

• Tanaka, N., et al.: J. Mol. Biol., 324, 519 (2002)
• Fitzpatrick, T., et al.: Biochem. J., 407, 1 (2002)
• Kalliri, E., et al.: J. Bacteriol., 190, 3793 (2002)