(1S,2R,3R)-1-{6-[(2S,3R)-2,3,4-trihydroxybutyl](2,3,5,6-13C4)pyrazin-2-yl}butane-1,2,3,4-tetrol

• ChemBase ID: 165949
• Molecular Formular: C12H20N2O7
• Molecular Mass: 308.26701935
• Monoisotopic Mass: 308.14047034
• SMILES: [13cH]1n[13cH][13c](n[13c]1C[C@@H]([C@@H](CO)O)O)[C@H]([C@@H]([C@@H](CO)O)O)O
• Canonical SMILES: OC[C@H]([C@H](C[13c]1[13cH]n[13cH][13c](n1)[C@H]([C@@H]([C@@H](CO)O)O)O)O)O
• InChI: InChI=1S/C12H20N2O7/c15-4-9(18)8(17)1-6-2-13-3-7(14-6)11(20)12(21)10(19)5-16/h2-3,8-12,15-21H,1,4-5H2/t8-,9+,10+,11+,12+/m0/s1/i2+1,3+1,6+1,7+1
• InChIKey: MBHUNOHYVYVNIP-ORHSJBJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,3R)-1-{6-[(2S,3R)-2,3,4-trihydroxybutyl](2,3,5,6-^1^3C₄)pyrazin-2-yl}butane-1,2,3,4-tetrol
• IUPAC Traditional name: (1S,2R,3R)-1-{6-[(2S,3R)-2,3,4-trihydroxybutyl](2,3,5,6-^1^3C₄)pyrazin-2-yl}butane-1,2,3,4-tetrol
• Synonyms: 1R,2S,3R)-1-[6-[(2S,3R)-2,3,4-Trihydroxybutyl]-2-pyrazinyl]-1,2,3,4-butanetetrol-13C4; 2-(D-arabino-1',2',3',4'-Tetrahydroxybutyl)-6-(D-erythro-2'',3'',4''-trihydroxybutyl)pyrazine-13C4; 2,6-Deoxyfructosazine-13C4

Database IDs

• PubChem SID: 162260082
• PubChem CID: 71315473

CALCULATED PROPERTIES

• Acid pKa: 12.28346
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -4.5963306
• LogD (pH = 7.4): -4.596333
• Log P: -4.596328
• Molar Refractivity: 68.9186 cm^3
• Polarizability: 27.78488 Å^3
• Polar Surface Area: 167.39 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Tan Solid
• Melting Point: 131-134°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D235802

Labelled 2,6-Deoxyfructosazine. Contained in tobacco flavor additives.

REFERENCES

• Tsuchida, H., et al.: Agric. Biol. Chem., 40, 921 (1976)