6-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine

• ChemBase ID: 179745
• Molecular Formular: C14H18N4O3
• Molecular Mass: 290.31772
• Monoisotopic Mass: 290.13789046
• SMILES: n1c(nc(cc1N)Cc1cc(c(c(c1)OC)OC)OC)N
• Canonical SMILES: COc1c(OC)cc(cc1OC)Cc1cc(N)nc(n1)N
• InChI: InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)13(10)21-3)4-9-7-12(15)18-14(16)17-9/h5-7H,4H2,1-3H3,(H4,15,16,17,18)
• InChIKey: ZQMPUWBQWRAQIQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
• IUPAC Traditional name: 6-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
• Synonyms: Isotrimethoprim

Database IDs

• CAS Number: 61550-88-7
• PubChem SID: 164235655
• PubChem CID: 452507

CALCULATED PROPERTIES

• Acid pKa: 16.976166
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.431436
• LogD (pH = 7.4): 0.89232963
• Log P: 1.1578233
• Molar Refractivity: 81.0856 cm^3
• Polarizability: 29.758389 Å^3
• Polar Surface Area: 105.51 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Dihydrofolate reductase inhibitor

Product Information

• Application(s): Antiseptic

REFERENCES

• Rosowsky A,Mota CE,Queener SF,Waltham M,Ercikan-Abali E,Bertino JR (1995) 2,4-Diamino-5-substituted-quinazolines as inhibitors of a human dihydrofolate reductase
• with a site-directed mutation at position 22 and of the dihydrofolate reductases from Pneumocystis carinii and Toxoplasma gondii. Journal of medicinal chemistry 38, 745-52