N-[4-({3-butyl-1-[(2-fluorophenyl)methyl]-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl}methyl)phenyl]acetamide

• ChemBase ID: 1775
• Molecular Formular: C25H26FN5O3
• Molecular Mass: 463.5040432
• Monoisotopic Mass: 463.20196794
• SMILES: O=C(C)Nc1ccc(cc1)Cc1nc2n(CCCC)c(=O)n(c(=O)c2[nH]1)Cc1ccccc1F
• Canonical SMILES: CCCCn1c2nc([nH]c2c(=O)n(c1=O)Cc1ccccc1F)Cc1ccc(cc1)NC(=O)C
• InChI: InChI=1S/C25H26FN5O3/c1-3-4-13-30-23-22(24(33)31(25(30)34)15-18-7-5-6-8-20(18)26)28-21(29-23)14-17-9-11-19(12-10-17)27-16(2)32/h5-12H,3-4,13-15H2,1-2H3,(H,27,32)(H,28,29)
• InChIKey: JHSHXKJSPVHPCJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[4-({3-butyl-1-[(2-fluorophenyl)methyl]-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl}methyl)phenyl]acetamide
• IUPAC Traditional name: N-[4-({3-butyl-1-[(2-fluorophenyl)methyl]-2,6-dioxo-7H-purin-8-yl}methyl)phenyl]acetamide
• Synonyms: N-[4-[[3-Butyl-1-[(2-fluorophenyl)methyl]-2,3,6,9-tetrahydro-2,6-dioxo-1H-purin-8-yl]methyl]phenyl]acetamide; N-[4-[1-(2-Fluorobenzyl)-3-butyl-2,6-dixo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]phenyl]acetamide; 1-(2-Fluorobenzyl)-3-Butyl-8-(N-Acetyl-4-Aminobenzyl)-Xanthine

Database IDs

• CAS Number: 628279-07-2
• PubChem SID: 160965231; 46504933
• PubChem CID: 447371

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.857844
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.6151993
• LogD (pH = 7.4): 3.5051873
• Log P: 3.6168673
• Molar Refractivity: 127.6627 cm^3
• Polarizability: 47.03535 Å^3
• Polar Surface Area: 98.4 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.63
• LOG S: -4.22
• Solubility (Water): 2.77e-02 g/l

DETAILS

DrugBank - DB02008

Drug information: experimental

Toronto Research Chemicals - F588520

It is used for the preparation of amide-substituted xanthine derivatives as phosphoenolpyruvate carboxykinase inhibitors with gluconeogenesis modulating activity for treating type 2 diabetes.

REFERENCES

• Kawashima, Y., et al.: Chem. Pharm. Bull., 43, 1132 (1995)
• Sun, Y., et al.: J. Biol. Chem., 277, 23301 (1995)
• Foley, L., et al.: Bioorg. Med. Chem. Lett., 13, 3871 (1995)