5-(2H5)ethyl-8-oxo-3-(pyrrolidin-1-yl)-5H,8H-pyrido[2,3-b]pyrazine-7-carboxylic acid

• ChemBase ID: 176794
• Molecular Formular: C14H16N4O3
• Molecular Mass: 288.30184
• Monoisotopic Mass: 288.12224039
• SMILES: c1(cnc2c(n1)n(cc(c2=O)C(=O)O)CC)N1CCCC1
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1nc(cn2)N1CCCC1
• InChI: InChI=1S/C14H16N4O3/c1-2-17-8-9(14(20)21)12(19)11-13(17)16-10(7-15-11)18-5-3-4-6-18/h7-8H,2-6H2,1H3,(H,20,21)
• InChIKey: JPKVGKXYVOPKKM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(^2H₅)ethyl-8-oxo-3-(pyrrolidin-1-yl)-5H,8H-pyrido[2,3-b]pyrazine-7-carboxylic acid
• IUPAC Traditional name: 5-(^2H₅)ethyl-8-oxo-3-(pyrrolidin-1-yl)pyrido[2,3-b]pyrazine-7-carboxylic acid
• Synonyms: 8-(Ethyl-d5)-5,8-dihydro-5-oxo-2-(1-pyrrolidinyl)pyrido[2,3-d]pyrimidine-6-carboxylic Acid; 5,8-Dihydro-8-(ethyl-d5)-5-oxo-2-pyrrolidinopyrido[2,3-d]pyrimidine-6-carboxylic Acid; Bactramyl-d5; Enterol-d5; Gastrurol-d5; NSC 291120-d5; PD 93-d5; Panacid-d5; Pirudal-d5; Purim-d5; Pyromidic Acid-d5; Reelon-d5; Septural-d5; Uropir-d5; Piromidic Acid-d5

Database IDs

• PubChem SID: 164232704
• PubChem CID: 71751701

CALCULATED PROPERTIES

• Acid pKa: 5.6348147
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 1.1444185
• LogD (pH = 7.4): -0.3820055
• Log P: 1.3831753
• Molar Refractivity: 77.9872 cm^3
• Polarizability: 28.184628 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P509502

Labelled Piromidic Acid (P509500). Quinolone antibacterial.

REFERENCES

• Shimizu, M., et al.: Antimicrob. Agents Chemother., 117, 1970,