{[(2R,4R,5S)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

• ChemBase ID: 169666
• Molecular Formular: C6H14NO8P
• Molecular Mass: 259.151021
• Monoisotopic Mass: 259.04570304
• SMILES: [C@@H]1([C@@H](C([C@H](OC1CO)OP(=O)(O)O)N)O)O
• Canonical SMILES: OCC1O[C@H](OP(=O)(O)O)C([C@H]([C@@H]1O)O)N
• InChI: InChI=1S/C6H14NO8P/c7-3-5(10)4(9)2(1-8)14-6(3)15-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2?,3?,4-,5-,6-/m1/s1
• InChIKey: YMJBYRVFGYXULK-YHMDAOSXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,4R,5S)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,4R,5S)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid
• Synonyms: 2-Amino-2-deoxy-α-D-glucopyranose 1-(dihydrogen phosphate); 2-Amino-2-deoxy-α-D-glucopyranosyl Phosphate; α-D-Glucosamine 1-Phosphate

Database IDs

• CAS Number: 2152-75-2
• PubChem SID: 162263798
• PubChem CID: 67796239

CALCULATED PROPERTIES

• Acid pKa: 1.1788105
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -4.2445183
• LogD (pH = 7.4): -5.353493
• Log P: -4.1756177
• Molar Refractivity: 48.4538 cm^3
• Polarizability: 20.562544 Å^3
• Polar Surface Area: 162.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G515060

A phosphorylated glucosamine used in the enzymatic α-glucosaminylation of maltooligosaccharides catalyzed by phosphorylase.

REFERENCES

• Nawaji, M. et al.: Carb. Res., 343, 2692 (2008)
• Batley, M. et al.: Biochem., 21, 6580 (2008)