tert-butyl N-(2-{[(tert-butoxy)carbonyl]amino}-5-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]pyrimidin-4-yl)carbamate

• ChemBase ID: 165756
• Molecular Formular: C23H32N4O7
• Molecular Mass: 476.52278
• Monoisotopic Mass: 476.22709938
• SMILES: c1(c(c(cc(c1)Cc1c(nc(nc1)NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)OC)O)OC
• Canonical SMILES: COc1cc(Cc2cnc(nc2NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)cc(c1O)OC
• InChI: InChI=1S/C23H32N4O7/c1-22(2,3)33-20(29)26-18-14(9-13-10-15(31-7)17(28)16(11-13)32-8)12-24-19(25-18)27-21(30)34-23(4,5)6/h10-12,28H,9H2,1-8H3,(H2,24,25,26,27,29,30)
• InChIKey: XPLGZFKYAQMIOD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-(2-{[(tert-butoxy)carbonyl]amino}-5-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]pyrimidin-4-yl)carbamate
• IUPAC Traditional name: tert-butyl N-{2-[(tert-butoxycarbonyl)amino]-5-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]pyrimidin-4-yl}carbamate
• Synonyms: N,N’-[5-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-2,4-pyrimidinediyl]bis-carbamic Acid C,C’-Bis(1,1-dimethylethyl) Ester; 4-Demethyl N,N'-Bis-Boc-Trimethoprim

Database IDs

• PubChem SID: 162259889
• PubChem CID: 71315375

CALCULATED PROPERTIES

• Acid pKa: 9.460859
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): 4.6177387
• LogD (pH = 7.4): 4.6140556
• Log P: 4.6177874
• Molar Refractivity: 128.2107 cm^3
• Polarizability: 47.84715 Å^3
• Polar Surface Area: 141.13 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D230925

A Trimethoprim (T795615) derivative.

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)