2-amino-5-[(3,4,5-trimethoxyphenyl)methyl]-3,4-dihydropyrimidin-4-one

• ChemBase ID: 160525
• Molecular Formular: C14H17N3O4
• Molecular Mass: 291.30248
• Monoisotopic Mass: 291.12190604
• SMILES: c1(c(c(cc(c1)Cc1c(=O)[nH]c(nc1)N)OC)OC)OC
• Canonical SMILES: COc1cc(Cc2cnc([nH]c2=O)N)cc(c1OC)OC
• InChI: InChI=1S/C14H17N3O4/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-16-14(15)17-13(9)18/h5-7H,4H2,1-3H3,(H3,15,16,17,18)
• InChIKey: ZKFZTBRMADDRMK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-5-[(3,4,5-trimethoxyphenyl)methyl]-3,4-dihydropyrimidin-4-one
• IUPAC Traditional name: 2-amino-5-[(3,4,5-trimethoxyphenyl)methyl]-3H-pyrimidin-4-one
• Synonyms: 2-Amino-5-(3,4,5-trimethoxybenzyl)-4-pyrimidinol; 2-Amino-5-[(3,4,5-trimethoxyphenyl)methyl]-4(1H)-pyrimidinone

Database IDs

• CAS Number: 92440-76-1
• PubChem SID: 162254660
• PubChem CID: 597783

CALCULATED PROPERTIES

• Acid pKa: 11.403215
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.70298773
• LogD (pH = 7.4): 0.7152491
• Log P: 0.71544653
• Molar Refractivity: 76.5912 cm^3
• Polarizability: 29.244059 Å^3
• Polar Surface Area: 95.17 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A630830

Degradation product/impurity of trimethoprim (T795615).

REFERENCES

• Roth, B., et al.: J., Med. Pharm. Chem., 5, 1103 (1962)
• Bergh, J., et al.: J. Pharm. Sci., 78, 348 (1962)