4-azido-2-hydroxy-N-{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl}benzamide

• ChemBase ID: 161044
• Molecular Formular: C13H16N4O7
• Molecular Mass: 340.28874
• Monoisotopic Mass: 340.10189887
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1CNC(=O)c1c(cc(cc1)N=[N+]=[N-])O)O)O)O)O
• Canonical SMILES: [N-]=[N+]=Nc1ccc(c(c1)O)C(=O)NC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C13H16N4O7/c14-17-16-5-1-2-6(7(18)3-5)12(22)15-4-8-9(19)10(20)11(21)13(23)24-8/h1-3,8-11,13,18-21,23H,4H2,(H,15,22)/t8-,9-,10+,11-,13?/m1/s1
• InChIKey: AMENESIYYZEZKA-TWEVDUBQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-azido-2-hydroxy-N-{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl}benzamide
• IUPAC Traditional name: 4-azido-2-hydroxy-N-{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl}benzamide
• Synonyms: 6-[(4-azido-2-hydroxybenzoyl)amino]-6-deoxy-D-glucose; ASA-GLC; N-(4-Azidosalicyl)-6-amido-6-deoxy-glucopyranose

Database IDs

• CAS Number: 86979-66-0
• PubChem SID: 162255179
• PubChem CID: 57357168

CALCULATED PROPERTIES

• Acid pKa: 7.6456833
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -0.7167091
• LogD (pH = 7.4): -0.9068845
• Log P: -0.5995957
• Molar Refractivity: 79.9637 cm^3
• Polarizability: 29.84736 Å^3
• Polar Surface Area: 168.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 183-185°C

DETAILS

Toronto Research Chemicals - A858000

Inhibits the labeling of the human erythrocyte monosaccharide transporter by [125I]IASA-glc more effectively that D-glucose.

REFERENCES

• Shanahan, M.F., The Journal of Biol. Chem., 260, 20, 10897 (1985)