[(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-[2-acetamido-3-methyl-3-(nitrososulfanyl)butanamido]oxan-2-yl]methyl acetate

• ChemBase ID: 175422
• Molecular Formular: C21H31N3O12S
• Molecular Mass: 549.54874
• Monoisotopic Mass: 549.16284445
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)OC(=O)C)NC(=O)C(C(SN=O)(C)C)NC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: O=NSC(C(C(=O)N[C@@H]1[C@H](OC(=O)C)O[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)COC(=O)C)NC(=O)C)(C)C
• InChI: InChI=1S/C21H31N3O12S/c1-9(25)22-18(21(6,7)37-24-31)19(30)23-15-17(34-12(4)28)16(33-11(3)27)14(8-32-10(2)26)36-20(15)35-13(5)29/h14-18,20H,8H2,1-7H3,(H,22,25)(H,23,30)/t14-,15-,16-,17-,18?,20-/m1/s1
• InChIKey: VISYVRBZWPNIOD-DYZQRANXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-[2-acetamido-3-methyl-3-(nitrososulfanyl)butanamido]oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-[2-acetamido-3-methyl-3-(nitrososulfanyl)butanamido]oxan-2-yl]methyl acetate
• Synonyms: 2-[[(2S)-2-(Acetylamino)-3-methyl-3-(nitrosothio)-1-oxobutyl]amino]-2-deoxy-β-D-glucopyranose 1,3,4,6-Tetraacetate; RIG200; N-(S-Nitroso-N-acetyl-D,L-penicillamine)-2-amino-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Database IDs

• CAS Number: 202656-49-3
• PubChem SID: 164231332
• PubChem CID: 9893746

CALCULATED PROPERTIES

• Acid pKa: 11.529617
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -0.8363795
• LogD (pH = 7.4): -0.83640754
• Log P: -0.836379
• Molar Refractivity: 122.9148 cm^3
• Polarizability: 49.520668 Å^3
• Polar Surface Area: 202.06 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N522540

Produced concentration-related relaxations of mouse anococcygeus, in a range similar to that already found for NO and other nitrovasodilators. A potent relaxant of non-vascular smooth muscle. Serves as an NO donor.

REFERENCES

• Miller, M.R., et al.: Eur. Journal of Pharmacology, 403, 111 (2000)