4-{[(2,4-diaminopteridin-6-yl)methyl](2H3)methylamino}benzoic acid

• ChemBase ID: 165292
• Molecular Formular: C15H15N7O2
• Molecular Mass: 325.3253
• Monoisotopic Mass: 325.12872276
• SMILES: c1(nc(nc2c1nc(cn2)CN(c1ccc(cc1)C(=O)O)C)N)N
• Canonical SMILES: Nc1nc(N)c2c(n1)ncc(n2)CN(c1ccc(cc1)C(=O)O)C
• InChI: InChI=1S/C15H15N7O2/c1-22(10-4-2-8(3-5-10)14(23)24)7-9-6-18-13-11(19-9)12(16)20-15(17)21-13/h2-6H,7H2,1H3,(H,23,24)(H4,16,17,18,20,21)
• InChIKey: LWCXZSDKANNOAR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(2,4-diaminopteridin-6-yl)methyl](^2H₃)methylamino}benzoic acid
• IUPAC Traditional name: 4-{[(2,4-diaminopteridin-6-yl)methyl](^2H₃)methylamino}benzoic acid
• Synonyms: 4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoic Acid-d3; 2,4-Diamino-N10-methylpteroic Acid-d3; 4-Amino-4-deoxy-10-methylpteroic Acid-d3; 4-Amino-4-deoxy-N10-methylpteroic Acid-d3; 4-Deoxy-4-amino-N10-methylpteroic Acid-d3; 4-[N-[(2,4-Diaminopyrimido[4,5-b]pyrazin-6-yl)methyl]-N-methylamino]benzoic Acid-d3; NSC 133723-d3; DAMPA-d3

Database IDs

• PubChem SID: 162259425
• PubChem CID: 71315111

CALCULATED PROPERTIES

• Acid pKa: 4.708153
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): 0.030896243
• LogD (pH = 7.4): -1.7467482
• Log P: 0.887536
• Molar Refractivity: 91.123 cm^3
• Polarizability: 32.656372 Å^3
• Polar Surface Area: 144.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D136502

Labelled Methotrexate (M260675) analog. DAMPA is an antitumor agent.

REFERENCES

• Martinelli, J.E., et al.: J. Med. Chem., 22, 869 (1979)