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

• ChemBase ID: 165958
• Molecular Formular: C13H23N3O8S
• Molecular Mass: 381.40202
• Monoisotopic Mass: 381.12058571
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1CO)O)NC(=O)C(C(C)(C)SN=O)NC(=O)C)O)O
• Canonical SMILES: O=NSC(C(C(=O)N[C@@H]1C(O)O[C@H]([C@H]([C@@H]1O)O)CO)NC(=O)C)(C)C
• InChI: InChI=1S/C13H23N3O8S/c1-5(18)14-10(13(2,3)25-16-23)11(21)15-7-9(20)8(19)6(4-17)24-12(7)22/h6-10,12,17,19-20,22H,4H2,1-3H3,(H,14,18)(H,15,21)/t6-,7-,8-,9-,10?,12?/m1/s1
• InChIKey: MPJKBQQBYUJGPA-OZXIJEGASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-acetamido-3-methyl-3-(nitrososulfanyl)-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]butanamide
• IUPAC Traditional name: 2-acetamido-3-methyl-3-(nitrososulfanyl)-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]butanamide
• Synonyms: 2-[[2-(Acetylamino)-3-methyl-3-(nitrosothio)-1-oxobutyl]amino]-2-deoxy-D-glucose; Glyco-SNAP-2; N-(2-Deoxy-α,β-D-glucopyranosyl)-S-nitroso-N-acetyl-D,L-penicillamine

Database IDs

• CAS Number: 188849-82-3
• PubChem SID: 162260091
• PubChem CID: 10407467

CALCULATED PROPERTIES

• Acid pKa: 11.339811
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.6008813
• LogD (pH = 7.4): -2.6009274
• 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 - D238120

Highly water 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)