4-{[(2-amino-4-oxo-4,8-dihydropteridin-6-yl)methyl](methyl)amino}benzoic acid

• ChemBase ID: 174269
• Molecular Formular: C15H14N6O3
• Molecular Mass: 326.31006
• Monoisotopic Mass: 326.11273834
• SMILES: n1c(nc2c(c1=O)nc(c[nH]2)CN(c1ccc(cc1)C(=O)O)C)N
• Canonical SMILES: Nc1nc(=O)c2c(n1)[nH]cc(n2)CN(c1ccc(cc1)C(=O)O)C
• InChI: InChI=1S/C15H14N6O3/c1-21(10-4-2-8(3-5-10)14(23)24)7-9-6-17-12-11(18-9)13(22)20-15(16)19-12/h2-6H,7H2,1H3,(H,23,24)(H3,16,17,19,20,22)
• InChIKey: QHNLFEQJGRZKTK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(2-amino-4-oxo-4,8-dihydropteridin-6-yl)methyl](methyl)amino}benzoic acid
• IUPAC Traditional name: 4-{[(2-amino-4-oxo-8H-pteridin-6-yl)methyl](methyl)amino}benzoic acid
• Synonyms: 4-[[(2-Amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]methylamino]benzoic Acid; p-[[(2-Amino-4-hydroxy-6-pteridinyl)methyl]methylamino]benzoic Acid; Metfol-B; NSC 408937; N10-Methyl Pteroic Acid

Database IDs

• CAS Number: 5623-18-7
• PubChem SID: 164230179
• PubChem CID: 21834

CALCULATED PROPERTIES

• Acid pKa: 4.708181
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -0.58844817
• LogD (pH = 7.4): -2.3880126
• Log P: 0.26842457
• Molar Refractivity: 86.9113 cm^3
• Polarizability: 31.450888 Å^3
• Polar Surface Area: 132.74 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M326265

Methotrexate (M260675) impurity D.

REFERENCES

• Cramer, S., et al.: Cancer Res. 1984, 44, 1843 (1984)
• Hendel, J., et al.: Eur. J. Clin. Pharmacol., 26, 103 (1984)