(2R,3S)-4-{benzo[g]quinoxalin-2-yl}butane-1,2,3-triol

• ChemBase ID: 161272
• Molecular Formular: C16H16N2O3
• Molecular Mass: 284.30984
• Monoisotopic Mass: 284.11609238
• SMILES: c1ccc2c(c1)cc1c(c2)ncc(n1)C[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H](Cc1cnc2c(n1)cc1c(c2)cccc1)O)O
• InChI: InChI=1S/C16H16N2O3/c19-9-16(21)15(20)7-12-8-17-13-5-10-3-1-2-4-11(10)6-14(13)18-12/h1-6,8,15-16,19-21H,7,9H2/t15-,16+/m0/s1
• InChIKey: UYVCNKANYYHWRW-JKSUJKDBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-4-{benzo[g]quinoxalin-2-yl}butane-1,2,3-triol
• IUPAC Traditional name: (2R,3S)-4-{benzo[g]quinoxalin-2-yl}butane-1,2,3-triol
• Synonyms: [S-(R*,S*)]-4-Benzo[g]quinoxalin-2-yl-1,2,3-butanetriol; 4-Benzo[g]quinoxalin-2-yl-1,2R,3S-Butanetriol

Database IDs

• CAS Number: 157231-41-9
• PubChem SID: 162255407
• PubChem CID: 29972614

CALCULATED PROPERTIES

• Acid pKa: 13.263978
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.57901657
• LogD (pH = 7.4): 0.5790195
• Log P: 0.5790201
• Molar Refractivity: 76.8187 cm^3
• Polarizability: 32.721554 Å^3
• Polar Surface Area: 86.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Hot Methanol (5mg / mL)
• Apperance: Yellow Solid
• Melting Point: 178-180°C

REFERENCES

• Yamada, H., et al.: J. Biol. Chem., 269, 20275 (1994)