2-amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic acid

• ChemBase ID: 164340
• Molecular Formular: C10H11ClN2O3
• Molecular Mass: 242.65894
• Monoisotopic Mass: 242.0458199
• SMILES: c1c(ccc(c1N)C(=O)CC(N)C(=O)O)Cl
• Canonical SMILES: OC(=O)C(CC(=O)c1ccc(cc1N)Cl)N
• 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)
• InChIKey: HQLHZNDJQSRKDT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic acid
• IUPAC Traditional name: 2-amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic acid
• Synonyms: α,2-Diamino-4-chloro-γ-oxobenzenebutanoic Acid; (+/-)-α,2-Diamino-4-chloro-γ-oxobenzenebutanoic Acid; 4-Cl-KYN; (+/-)-AV-101; 4-Chloro Kynurenine

Database IDs

• CAS Number: 75802-84-5
• PubChem SID: 162258475
• PubChem CID: 173480

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

DETAILS

Toronto Research Chemicals - C366940

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)