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

• ChemBase ID: 177107
• Molecular Formular: C14H12N6O3
• Molecular Mass: 312.28348
• Monoisotopic Mass: 312.09708827
• SMILES: n1c(nc2c(c1=O)nc(c[nH]2)CNc1ccc(cc1)C(=O)O)N
• Canonical SMILES: Nc1nc(=O)c2c(n1)[nH]cc(n2)CNc1ccc(cc1)C(=O)O
• InChI: InChI=1S/C14H12N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,6,16H,5H2,(H,22,23)(H3,15,17,19,20,21)
• InChIKey: JOAQINSXLLMRCV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(2-amino-4-oxo-4,8-dihydropteridin-6-yl)methyl]amino}benzoic acid
• IUPAC Traditional name: 4-{[(2-amino-4-oxo-8H-pteridin-6-yl)methyl]amino}benzoic acid
• Synonyms: 4-[[(2-Amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoic Acid; NSC 14972; Pyrofolic acid; p-[(2-Amino-4-hydroxy-6-pteridylmethyl)amino]benzoic Acid; Pteroic Acid

Database IDs

• CAS Number: 119-24-4
• PubChem SID: 164233017
• PubChem CID: 95054

CALCULATED PROPERTIES

• Acid pKa: 4.7224073
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.2133107
• LogD (pH = 7.4): -3.0109398
• Log P: -0.36684114
• Molar Refractivity: 82.6765 cm^3
• Polarizability: 29.62583 Å^3
• Polar Surface Area: 141.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P840110

Pteroic Acid is a constituent as well as a degradation product of Folid Acid (F680300) formed via anzymatic hydrolysis. has been shown to activate the glutamylation of methotrexate by folylpolyglutamate synthetase.

REFERENCES

• Vickers, P.J. et al.: Can. J. Biochem. Cell Biol., 63, 777 (1985): Tafolla, W.H. et al.: J. Pharmac. Sci., 70, 1273 (1981)
• Iwai, K. et al.: J. Butrit. Sci. Vitaminol., 23, 95 (1981)