2-amino-4-(2-amino-4-chlorophenyl)-4-oxo(1,2-13C2)butanoic acid

• ChemBase ID: 164341
• Molecular Formular: C10H11ClN2O3
• Molecular Mass: 245.63765857
• Monoisotopic Mass: 245.04956447
• SMILES: c1c(ccc(c1N)C(=O)C[13CH]([15NH2])[13C](=O)O)Cl
• Canonical SMILES: O[13C](=O)[13CH](CC(=O)c1ccc(cc1N)Cl)[15NH2]
• InChI: InChI=1S/C10H11ClN2O3/c11-5-1-2-6(7(12)3-5)9(14)4-8(13)10(15)16/h1-3,8H,4,12-13H2,(H,15,16)/i8+1,10+1,13+1
• InChIKey: HQLHZNDJQSRKDT-SVKOXWCPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(2-amino-4-chlorophenyl)-4-oxo(1,2-^1^3C₂)butanoic acid
• IUPAC Traditional name: 2-amino-4-(2-amino-4-chlorophenyl)-4-oxo(1,2-^1^3C₂)butanoic acid
• Synonyms: α,2-Diamino-4-chloro-γ-oxobenzenebutanoic Acid-13C2,15N; (+/-)-α,2-Diamino-4-chloro-γ-oxobenzenebutanoic Acid-13C2,15N; 4-Cl-KYN-13C2,15N; (+/-)-AV-101-13C2,15N; 4-Chloro Kynurenine-13C2,15N

Database IDs

• PubChem SID: 162258476
• PubChem CID: 71314743

CALCULATED PROPERTIES

• Acid pKa: 0.92498934
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.3038341
• LogD (pH = 7.4): -1.3144238
• Log P: -1.3039242
• Molar Refractivity: 59.855 cm^3
• Polarizability: 22.890831 Å^3
• Polar Surface Area: 106.41 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Acid; Aqueous Base
• Apperance: Pale Yellow Solid
• Melting Point: >205°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C366942

7-Cl-kynurenic acid (7-Cl-KYNA) is a potent, selective antagonist of the NMDA/glycine receptor but penetrates poorly through the blood-brain barrier. Its prodrug, L-4-Cl-kynurenine (4-Cl-KYN), readily enters the brain from the circulation and provides antiexcitotoxic neuroprotection after systemic application.

REFERENCES

• Leeson, P., et al.: J. Med. Chem., 37, 4053 (1994)
• Hilmas, C., et al.: J. Neurosci., 2001, 21, 7463 (1994)
• Palmer, G., et al.: Curr. Drug Targets, 2, 241 (1994)
• Wu, H., et al.: Exp. Neurol., 177, 222 (1994)