dihydroxy(2H4)quinoline-2-carboxylic acid

• ChemBase ID: 179598
• Molecular Formular: C10H7NO4
• Molecular Mass: 205.16688
• Monoisotopic Mass: 205.03750771
• SMILES: c1cc(c2c(c1)c(cc(n2)C(=O)O)O)O
• Canonical SMILES: OC(=O)c1cc(O)c2c(n1)c(O)ccc2
• InChI: InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)
• InChIKey: FBZONXHGGPHHIY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dihydroxy(^2H₄)quinoline-2-carboxylic acid
• IUPAC Traditional name: dihydroxy(^2H₄)quinoline-2-carboxylic acid
• Synonyms: 4,8-Dihydroxy-2-quinolinecarboxylic Acid-d4; 4,8-Dihydroxyquinaldic Acid-d4; 8-Hydroxykynurenic Acid-d4; NSC 401570-d4; Xanthuric Acid-d4; Xanthurenic Acid-d4

Database IDs

• PubChem SID: 164235508
• PubChem CID: 71753000

CALCULATED PROPERTIES

• Acid pKa: 1.1175392
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.32295325
• LogD (pH = 7.4): -1.7002906
• Log P: 0.07666184
• Molar Refractivity: 50.8253 cm^3
• Polarizability: 20.532118 Å^3
• Polar Surface Area: 90.65 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - X743502

Labelled Xanthurenic Acid (X743500). Excreted by pyridoxine-deficient animals after the ingestion of tryptophan.

REFERENCES

• Aquilina, J., et al.: Biochemistry, 39, 16176 (2000)
• Roberts, J., et al.: Photochem. Photobiol., 74, 740 (2000)