2-acetamido-3-methyl-3-(nitrososulfanyl)-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]butanamide

• ChemBase ID: 169655
• Molecular Formular: C13H23N3O8S
• Molecular Mass: 381.40202
• Monoisotopic Mass: 381.12058571
• SMILES: C(=O)(C(C(SN=O)(C)C)NC(=O)C)N[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)O
• Canonical SMILES: O=NSC(C(C(=O)N[C@@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1O)O)O)NC(=O)C)(C)C
• InChI: InChI=1S/C13H23N3O8S/c1-5(18)14-10(13(2,3)25-16-23)11(22)15-12-9(21)8(20)7(19)6(4-17)24-12/h6-10,12,17,19-21H,4H2,1-3H3,(H,14,18)(H,15,22)/t6-,7-,8+,9-,10?,12-/m1/s1
• InChIKey: QNMMQEFPNFRVFP-HCTIOZQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-acetamido-3-methyl-3-(nitrososulfanyl)-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]butanamide
• IUPAC Traditional name: 2-acetamido-3-methyl-3-(nitrososulfanyl)-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]butanamide
• Synonyms: 2-(Acetylamino)-N-β-D-glucopyranosyl-3-methyl-3-(nitrosothio)butanamide; Glyco-SNAP-1; N-(β-Glucopyranosyl)-N2-acetyl-S-nitrosopenicillamide; N-(β-D-Glucopyranosyl)-N2-acetyl-S-nitroso-D,L-penicillamide

Database IDs

• CAS Number: 214193-25-6
• PubChem SID: 162263787
• PubChem CID: 10385174

CALCULATED PROPERTIES

• Acid pKa: 11.15191
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.6008816
• LogD (pH = 7.4): -2.6009493
• Log P: -2.6008806
• Molar Refractivity: 86.3088 cm^3
• Polarizability: 34.095222 Å^3
• Polar Surface Area: 177.78 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Green Solid

DETAILS

Toronto Research Chemicals - G419525

N-(β-D-Glucopyranosyl)-N2-acetyl-S-nitroso-D,L-penicillamide is a highly soluble nitric oxide donor, which is relatively stable at high pH (pH 8-9).

REFERENCES

• Ramirez, J., et al.: Bioorg. Med. Chem. Lett, 6, 2575 (1996)
• Wu, J., et al.: J. Lipid Res., 46, 1944 (1996)
• Shuji, O., et al.: Biomed. Res., 28, 91 (1996)