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

• ChemBase ID: 165363
• Molecular Formular: C16H17N7O2
• Molecular Mass: 339.35188
• Monoisotopic Mass: 339.14437282
• SMILES: c1(nc(nc2c1nc(cn2)CN(c1ccc(cc1)C(=O)OC)C)N)N
• Canonical SMILES: COC(=O)c1ccc(cc1)N(Cc1cnc2c(n1)c(N)nc(n2)N)C
• InChI: InChI=1S/C16H17N7O2/c1-23(11-5-3-9(4-6-11)15(24)25-2)8-10-7-19-14-12(20-10)13(17)21-16(18)22-14/h3-7H,8H2,1-2H3,(H4,17,18,19,21,22)
• InChIKey: FBFNJDZYIIOJMK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoate
• IUPAC Traditional name: methyl 4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoate
• Synonyms: 4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoic Acid Methyl Ester; Methyl 4-Amino-4-deoxy-10-methyl Pteroate; NSC 133722; DAMPA Methyl Ester

Database IDs

• CAS Number: 23853-09-0
• PubChem SID: 162259496
• PubChem CID: 281163

CALCULATED PROPERTIES

• Acid pKa: 15.865532
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 1.2333426
• LogD (pH = 7.4): 1.233429
• Log P: 1.23343
• Molar Refractivity: 95.8921 cm^3
• Polarizability: 34.73571 Å^3
• Polar Surface Area: 133.14 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: .250°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D136525

A Methotrexate analog with altered ester group.

REFERENCES

• Homma, A., et al.: Bioorg. Med. Chem., 17, 4647 (2009)
• Banjanac, M., et al.: Food Technol. Biotechnol., 47, 236 (2009)