5-(2H5)ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid

• ChemBase ID: 176021
• Molecular Formular: C13H11NO5
• Molecular Mass: 261.23014
• Monoisotopic Mass: 261.06372246
• SMILES: c12c(cc3c(c1)n(cc(c3=O)C(=O)O)CC)OCO2
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1cc1OCOc1c2
• InChI: InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)
• InChIKey: KYGZCKSPAKDVKC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(^2H₅)ethyl-8-oxo-2H,5H,8H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
• IUPAC Traditional name: 5-(^2H₅)ethyl-8-oxo-2H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
• Synonyms: 5-(Ethyl-d5)-5,8-dihydro-8-oxo-1,3-Dioxolo[4,5-g]quinoline-7-carboxylic Acid; 1-(Ethyl-d5)-6,7-methylenedioxy-4-quinolone-3-carboxylic Acid; NSC 110364-d5; Nidantin-d5; Ossian-d5; Oxoboi-d5; Pietil-d5; Prodoxal-d5; Uritrate-d5; Urotrate-d5; W 4565-d5; Oxolinic Acid-d5

Database IDs

• PubChem SID: 164231931
• PubChem CID: 46782642

CALCULATED PROPERTIES

• Acid pKa: 5.579866
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.0903233
• LogD (pH = 7.4): -0.46510977
• Log P: 1.3531469
• Molar Refractivity: 65.8433 cm^3
• Polarizability: 24.67664 Å^3
• Polar Surface Area: 76.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Hot Alkali; Hot Water
• Apperance: Tan Solid
• Melting Point: 318-320°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - O857502

Labelled quinolone antibacterial.

REFERENCES

• DiCarlo, et al.: Arch. Biochem. Biophys., 127, 503 (1968)
• Crew, et al.: Xenobiotica, 1, 193 (1968)
• Wright, H.T., et al.: Science, 213, 455 (1968)