potassium 4-[3-(6-oxo-6,9-dihydro-1H-purin-9-yl)propanamido]benzoate

• ChemBase ID: 172268
• Molecular Formular: C15H12KN5O4
• Molecular Mass: 365.38518
• Monoisotopic Mass: 365.05263557
• SMILES: [nH]1cnc2c(c1=O)ncn2CCC(=O)Nc1ccc(cc1)C(=O)[O-].[K+]
• Canonical SMILES: O=C(Nc1ccc(cc1)C(=O)[O-])CCn1cnc2c1nc[nH]c2=O.[K+]
• InChI: InChI=1S/C15H13N5O4.K/c21-11(19-10-3-1-9(2-4-10)15(23)24)5-6-20-8-18-12-13(20)16-7-17-14(12)22;/h1-4,7-8H,5-6H2,(H,19,21)(H,23,24)(H,16,17,22);/q;+1/p-1
• InChIKey: MICLTPPSCUXHJT-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium 4-[3-(6-oxo-6,9-dihydro-1H-purin-9-yl)propanamido]benzoate
• IUPAC Traditional name: potassium 4-[3-(6-oxo-1H-purin-9-yl)propanamido]benzoate
• Synonyms: 4-[[3-(1,6-Dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoic Acid Potassium Salt; AIT 082; Neotrofin; Leteprinim Potassium Salt

Database IDs

• CAS Number: 192564-13-9
• PubChem SID: 164228178
• PubChem CID: 23663995

CALCULATED PROPERTIES

• Acid pKa: 4.1605606
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.2444394
• LogD (pH = 7.4): -2.9588253
• Log P: 0.11197002
• Molar Refractivity: 96.7868 cm^3
• Polarizability: 30.511827 Å^3
• Polar Surface Area: 128.51 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off White to Pale Yellow Solid
• Melting Point: 268-270°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - L329900

A synthetic purine derivative with neuroprotective effects. A cognitive enhancer, is transported into brain by a nonsaturable influx mechanism and out of brain by a saturable efflux mechanism.

REFERENCES

• Cornford, E., et al.: Biochim. Biophys. Acta, 394, 211 (1975)
• Middlemiss, P., et al.: Neurosci. Lett., 199, 131 (1975)
• Rathbone, M., et al.: Drug Dev. Res., 45, 356 (1975)
• Rathbone, M., et al.: Exp. Opin. Invest. Drugs, 8, 1255 (1975)
• Yan, R., et al.: