(2R,3R,5R)-2-(aminomethyl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 159723
• Molecular Formular: C6H13NO4
• Molecular Mass: 163.17172
• Monoisotopic Mass: 163.0844579
• SMILES: [C@@H]1(C([C@H](O[C@@H]1CN)CO)O)O
• Canonical SMILES: NC[C@H]1O[C@@H](C([C@@H]1O)O)CO
• InChI: InChI=1S/C6H13NO4/c7-1-3-5(9)6(10)4(2-8)11-3/h3-6,8-10H,1-2,7H2/t3-,4-,5+,6?/m1/s1
• InChIKey: IKPYGNYNWRCKKG-VRPWFDPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-2-(aminomethyl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,5R)-2-(aminomethyl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 1-Amino-2,5-anhydro-D-mannitol; 1-Amino-2,5-anhydro-1-deoxy-D-mannitol

Database IDs

• CAS Number: 228862-97-3
• PubChem SID: 162253858
• PubChem CID: 45038104

CALCULATED PROPERTIES

• Acid pKa: 12.777172
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -5.520595
• LogD (pH = 7.4): -4.081727
• Log P: -2.6751971
• Molar Refractivity: 36.551 cm^3
• Polarizability: 15.257229 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Yellow to Light Brown Oil

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A582100

1-Amino-2,5-anhydro-1-deoxy-D-mannitol , a β-D-fructose analog, serves as a substrate for the hexose transporter of Trypanosoma brucei, while the human erythrocyte transporter can only use D-glucose.

REFERENCES

• Claustre, S., et al.: Carbohydrate Res., 315, 339-344 (1999)
• Yang, J., et al.: Biochem. J., 367, 533 (1999)