ethyl 4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoate

• ChemBase ID: 165293
• Molecular Formular: C17H19N7O2
• Molecular Mass: 353.37846
• Monoisotopic Mass: 353.16002288
• SMILES: c1(nc(nc2c1nc(cn2)CN(c1ccc(cc1)C(=O)OCC)C)N)N
• Canonical SMILES: CCOC(=O)c1ccc(cc1)N(Cc1cnc2c(n1)c(N)nc(n2)N)C
• InChI: InChI=1S/C17H19N7O2/c1-3-26-16(25)10-4-6-12(7-5-10)24(2)9-11-8-20-15-13(21-11)14(18)22-17(19)23-15/h4-8H,3,9H2,1-2H3,(H4,18,19,20,22,23)
• InChIKey: BDYWKUSEZMEPPR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoate
• IUPAC Traditional name: ethyl 4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoate
• Synonyms: 4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoic Acid Ethyl Ester; Ethyl p-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoate; NSC 694477; DAMPA Ethyl Ester

Database IDs

• CAS Number: 43111-51-9
• PubChem SID: 162259426
• PubChem CID: 393093

CALCULATED PROPERTIES

• Acid pKa: 15.865532
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 1.5901506
• LogD (pH = 7.4): 1.5902369
• Log P: 1.590238
• Molar Refractivity: 100.6407 cm^3
• Polarizability: 36.571228 Å^3
• Polar Surface Area: 133.14 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - D136515

A Methotrexate analog with altered ester group.

REFERENCES

• Rabow, A., et al.: J. Med. Chem., 45, 818 (2002)