2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid

• ChemBase ID: 155062
• Molecular Formular: C14H8N2O6
• Molecular Mass: 300.22312
• Monoisotopic Mass: 300.03823599
• SMILES: c1cc(c2c(c1)oc1cc(=O)c(c(c1n2)C(=O)O)N)C(=O)O
• Canonical SMILES: OC(=O)c1c2nc3c(oc2cc(=O)c1N)cccc3C(=O)O
• InChI: InChI=1S/C14H8N2O6/c15-10-6(17)4-8-12(9(10)14(20)21)16-11-5(13(18)19)2-1-3-7(11)22-8/h1-4H,15H2,(H,18,19)(H,20,21)
• InChIKey: FSBKJYLVDRVPTK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid
• IUPAC Traditional name: cinnabarinic acid
• Synonyms: 2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid; Cinnabaric acid; Cinnabarinic Acid; Cinnabarinic Acid

Database IDs

• CAS Number: 606-59-7
• MDL Number: MFCD18379297
• PubChem SID: 162249200
• PubChem CID: 114918

CALCULATED PROPERTIES

• Acid pKa: 2.366797
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -4.1744657
• LogD (pH = 7.4): -6.306616
• Log P: 0.43857545
• Molar Refractivity: 76.8991 cm^3
• Polarizability: 26.908531 Å^3
• Polar Surface Area: 139.28 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: ≥4 mg/mL; Methanol
• Apperance: Dark Red Solid; red to very dark red powder
• Melting Point: >300°C

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H8N2O6

DETAILS

Sigma Aldrich - SML0096

Biochem/physiol Actions
Cinnabarinic acid is a kynurenine pathway metabolite of tryptophan, produced by the oxidation of 3-Hydroxyanthranilic acid. Cinnabarinic acid leads to loss of mitochondrial respiration and apoptosis, and has also been shown to be an mGlu4R-specific agonist.

Toronto Research Chemicals - C442000

A natural phenoxazinone derivative, Cinnabarinic acid is obtained in vitro with aid of laccase by oxidative dimerization of 3-Hydroxyanthranilic acid (a metabolite of the amino acid Trytophan). Cinnabarinic acid strongly induces apoptosis in thymocytes th

REFERENCES

• Osiadacz, J., et al.: J. Biotechnol., 72, 141 (1999)
• Kumar, D., et al.: Bioorg. Med. Chem., 10, 3997 (1999)
• McCleland, B., et al.: Bioorg. Med. Chem. Lett., 17, 1713 (1999)