N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-[hydroxy(13C)methyl](2,3,4,5,6-13C5)oxan-3-yl]acetamide

• ChemBase ID: 159284
• Molecular Formular: C8H15NO6
• Molecular Mass: 227.16372903
• Monoisotopic Mass: 227.11006623
• SMILES: [13C@@H]1([13C@@H]([13C@@H]([13CH](O[13C@H]1[13CH2]O)O)NC(=O)C)O)O
• Canonical SMILES: O[13CH2][13C@@H]1O[13CH](O)[13C@H]([13C@H]([13C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8?/m1/s1/i2+1,4+1,5+1,6+1,7+1,8+1
• InChIKey: OVRNDRQMDRJTHS-ZEUBEQSHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-[hydroxy(^1^3C)methyl](2,3,4,5,6-^1^3C₅)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-[hydroxy(^1^3C)methyl](2,3,4,5,6-^1^3C₅)oxan-3-yl]acetamide
• Synonyms: 2-(Acetylamino)-2-deoxy-D-glucose-13C6; 2-Acetamido-2-deoxy-D-glucose-13C6; NSC 524344-13C6; N-Acetyl-D-glucosamine-13C6

Database IDs

• PubChem SID: 162253419
• PubChem CID: 71312896

CALCULATED PROPERTIES

• Acid pKa: 11.60413
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.2205749
• LogD (pH = 7.4): -3.2206008
• Log P: -3.2205744
• Molar Refractivity: 47.0247 cm^3
• Polarizability: 19.398714 Å^3
• Polar Surface Area: 119.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A178003

A labelled pharmaceutical and cosmetic sugar.

REFERENCES

• Rossi, V., et al.: J, Biol. Chem., 273, 1232 (1998)
• Fyfe, J., et al.: Blood, 103, 1573 (1998)
• Latge, J., et al.: Mol. Microbiol., 66, 279 (1998)
• Reese, T., et al.: Nature, 447, 92 (1998)