5-{[4,5-bis(2H3)methoxy-2-methylphenyl]methyl}pyrimidine-2,4-diamine

• ChemBase ID: 175930
• Molecular Formular: C14H18N4O2
• Molecular Mass: 274.31832
• Monoisotopic Mass: 274.14297584
• SMILES: c1c(c(cc(c1C)Cc1cnc(nc1N)N)OC)OC
• Canonical SMILES: COc1cc(Cc2cnc(nc2N)N)c(cc1OC)C
• InChI: InChI=1S/C14H18N4O2/c1-8-4-11(19-2)12(20-3)6-9(8)5-10-7-17-14(16)18-13(10)15/h4,6-7H,5H2,1-3H3,(H4,15,16,17,18)
• InChIKey: KEEYRKYKLYARHO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[4,5-bis(^2H₃)methoxy-2-methylphenyl]methyl}pyrimidine-2,4-diamine
• IUPAC Traditional name: 5-{[4,5-bis(^2H₃)methoxy-2-methylphenyl]methyl}pyrimidine-2,4-diamine
• Synonyms: 2,4-Diamino-5-(6-methylveratryl)pyrimidine-d6; 2,4-Diamino-5-[2-methyl-4,5-(dimethoxy-d6)benzyl]pyrimidine; Diamino-5-(6-methylveratryl)pyrimidine-d6; NSC 95072-d6; Ormethoprim-d6; Ro 5-9754-d6; Ormetoprim-d6

Database IDs

• PubChem SID: 164231840
• PubChem CID: 71751340

CALCULATED PROPERTIES

• Acid pKa: 17.336613
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.6912727
• LogD (pH = 7.4): 1.7672775
• Log P: 1.955
• Molar Refractivity: 80.0874 cm^3
• Polarizability: 28.98327 Å^3
• Polar Surface Area: 96.28 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O686802

Labelled O686800 (O686800). It is a potent and selective inhibitor of bacterial dihydrofolate reductase, the enzyme responsible for the NADPH-dependent reduction of 7,8-dihydrofolate to 5,6,7,8-tetrahydrofolate. Antibacterial.

REFERENCES

• Manius, G.J., et al.: Anal. Profiles Drug Subs., 7, 445 (1978)
• Roth, B., et al.: J. Med. Chem., 23, 379 (1978)
• Brogden, R.N., et al.: Drugs, 23, 405 (1978)