(2S)-2-acetamido-3-methyl-3-(nitrososulfanyl)-N-{[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}butanamide

• ChemBase ID: 169472
• Molecular Formular: C13H23N3O8S
• Molecular Mass: 381.40202
• Monoisotopic Mass: 381.12058571
• SMILES: [C@H]1([C@@](OC[C@H]([C@@H]1O)O)(O)CNC(=O)[C@@H](C(SN=O)(C)C)NC(=O)C)O
• Canonical SMILES: O[C@H]1[C@@H](O)[C@H](O)CO[C@]1(O)CNC(=O)[C@@H](C(SN=O)(C)C)NC(=O)C
• InChI: InChI=1S/C13H23N3O8S/c1-6(17)15-9(12(2,3)25-16-23)11(21)14-5-13(22)10(20)8(19)7(18)4-24-13/h7-10,18-20,22H,4-5H2,1-3H3,(H,14,21)(H,15,17)/t7-,8-,9+,10+,13-/m1/s1
• InChIKey: PZUYSUGHXUBVOG-JJKYCLHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-acetamido-3-methyl-3-(nitrososulfanyl)-N-{[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}butanamide
• IUPAC Traditional name: (2S)-2-acetamido-3-methyl-3-(nitrososulfanyl)-N-{[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methyl}butanamide
• Synonyms: Fructose-1-SNAP; 1-[[(2S)-2-(Acetylamino)-3-methyl-3-(nitrosothio)-1-oxobutyl]amino]-1-deoxy-β-D-Fructopyranose; Fructose-1-S-nitroso-N-acetyl-D,L-penicillamine

Database IDs

• CAS Number: 330688-79-4
• PubChem SID: 162263604
• PubChem CID: 10362424

CALCULATED PROPERTIES

• Acid pKa: 10.628269
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.4263442
• LogD (pH = 7.4): -2.4265954
• Log P: -2.4263408
• Molar Refractivity: 86.7462 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

• Apperance: Green Powder

DETAILS

Toronto Research Chemicals - F795500

A nitric oxide donor with enhanced cytotoxicity to DU-145 human prostate cancers in vitro.

REFERENCES

• Hou, Y., et al.: Tetrahedron Letters, 42, 825 (2001)