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

• ChemBase ID: 132165
• Molecular Formular: C12H20N2O8
• Molecular Mass: 320.2958
• Monoisotopic Mass: 320.12196561
• SMILES: O[C@H](c1ncc(nc1)[C@@H](O)[C@H](O)[C@H](O)CO)[C@H](O)[C@H](O)CO
• Canonical SMILES: OC[C@H]([C@H]([C@@H](c1ncc(nc1)[C@H]([C@@H]([C@@H](CO)O)O)O)O)O)O
• InChI: InChI=1S/C12H20N2O8/c15-3-7(17)11(21)9(19)5-1-13-6(2-14-5)10(20)12(22)8(18)4-16/h1-2,7-12,15-22H,3-4H2/t7-,8-,9-,10-,11-,12-/m1/s1
• InChIKey: NPWQIVOYGNUVEB-PAUJSFGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3R)-1-{5-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]pyrazin-2-yl}butane-1,2,3,4-tetrol
• IUPAC Traditional name: (1R,2S,3R)-1-{5-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]pyrazin-2-yl}butane-1,2,3,4-tetrol
• Synonyms: (1R,1'R,2S,2'S,3R,3'R)-1,1'-(2,5-Pyrazinediyl)bis-1,2,3,4-butanetetrol; D-Arabino-1,1'-(2,5-pyrazinediyl)di-1,2,3,4-butanetetrol; Fructosazine; 2,5-bis(D-Arabinotetrahydroxybutyl)pyrazine; Fructosazine

Database IDs

• CAS Number: 13185-73-4
• PubChem SID: 162226442
• PubChem CID: 493590

CALCULATED PROPERTIES

• Acid pKa: 12.010453
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -5.311487
• LogD (pH = 7.4): -5.3114967
• Log P: -5.3114862
• Molar Refractivity: 70.2568 cm^3
• Polarizability: 28.553135 Å^3
• Polar Surface Area: 187.62 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White to Pale Beige Solid
• Melting Point: >150°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3

DETAILS

Toronto Research Chemicals - F785000

Used in the treatment of osteoarthritis and rheumatoid arthritis.

REFERENCES

• Yamaguchi, T., et al.: Biol. Pharm. Bull., 21, 205 (1998)
• Fenton, J., et al.: Osteoarthritis Cartilage, 8, 444 (1998)
• Shimamura, T., et al.: J. Agric. Food. Chem., 48, 1204 (2000)