2-{[1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]formamido}acetic acid

• ChemBase ID: 169782
• Molecular Formular: C17H17FN2O5
• Molecular Mass: 348.3256832
• Monoisotopic Mass: 348.11214987
• SMILES: c1c(cc2c(c1)n(c(=O)c(c2O)C(=O)NCC(=O)O)CCC1CC1)F
• Canonical SMILES: OC(=O)CNC(=O)c1c(O)c2cc(F)ccc2n(c1=O)CCC1CC1
• InChI: InChI=1S/C17H17FN2O5/c18-10-3-4-12-11(7-10)15(23)14(16(24)19-8-13(21)22)17(25)20(12)6-5-9-1-2-9/h3-4,7,9,23H,1-2,5-6,8H2,(H,19,24)(H,21,22)
• InChIKey: TYHRZQVUPPODPT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]formamido}acetic acid
• IUPAC Traditional name: {[1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-2-oxoquinolin-3-yl]formamido}acetic acid
• Synonyms: N-[[1-(2-Cyclopropylethyl)-6-fluoro-1,2-dihydro-4-hydroxy-2-oxo-3-quinolinyl]carbonyl]glycine; N-[[1-(2-Cyclopropylethyl)-6-fluoro-4-hydroxy-2-oxo-1,2-dihydro-3-quinolinyl]carbonyl]glycine; GSK360A

Database IDs

• CAS Number: 931399-19-8
• PubChem SID: 162263914
• PubChem CID: 54685147

CALCULATED PROPERTIES

• Acid pKa: 3.308954
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.9496487
• LogD (pH = 7.4): -4.718548
• Log P: 0.4795155
• Molar Refractivity: 86.0016 cm^3
• Polarizability: 32.330605 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Beige Solid
• Melting Point: 195-197°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - G797600

GSK360A orally active HIF-PHD inhibitor. GSK360A exerts systemic and local effects by stabilizing HIF-1α signaling and improves long-term ventricular function, remodeling, and vascularity in a model of established ventricular dysfunction. These findings s

REFERENCES

• Bao, W.-K. et al.: J. Cardio. Pharmacol., 56, 147 (2010)