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

• ChemBase ID: 165950
• Molecular Formular: C12H20N2O7
• Molecular Mass: 304.2964
• Monoisotopic Mass: 304.12705099
• SMILES: c1(ncc(nc1)[C@H]([C@@H]([C@@H](CO)O)O)O)C[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H](Cc1ncc(nc1)[C@H]([C@@H]([C@@H](CO)O)O)O)O)O
• InChI: InChI=1S/C12H20N2O7/c15-4-9(18)8(17)1-6-2-14-7(3-13-6)11(20)12(21)10(19)5-16/h2-3,8-12,15-21H,1,4-5H2/t8-,9+,10+,11+,12+/m0/s1
• InChIKey: FBDICDJCXVZLIP-VSSNEEPJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3R)-1-{5-[(2S,3R)-2,3,4-trihydroxybutyl]pyrazin-2-yl}butane-1,2,3,4-tetrol
• IUPAC Traditional name: (1R,2S,3R)-1-{5-[(2S,3R)-2,3,4-trihydroxybutyl]pyrazin-2-yl}butane-1,2,3,4-tetrol
• Synonyms: (1R,2S,3R)-1-[5-[(2S,3R)-2,3,4-Trihydroxybutyl]-2-pyrazinyl]-1,2,3,4-butanetetrol; 2-(D-arabino-Tetrahydroxybutyl)-5-(D-erythro-2,3,4-trihydroxybutyl)pyrazine; NSC 270912; 2,5-Deoxyfructosazine

Database IDs

• CAS Number: 17460-13-8
• PubChem SID: 162260083
• PubChem CID: 73452

CALCULATED PROPERTIES

• Acid pKa: 12.293576
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -4.596331
• LogD (pH = 7.4): -4.596333
• Log P: -4.596328
• Molar Refractivity: 68.9186 cm^3
• Polarizability: 27.784863 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: 157-160°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D235810

Contained in tobacco flavor additives.

REFERENCES

• Sumoto, K., et al.: Chem. Pharm. Bull., 39, 792 (1991)
• Shimamura, T., et al.: Biosci., Biotechnol., Biochem., 67, 295 (1991)