(2S)-2-[(4-{N-[(2-amino-4-oxo-4,8-dihydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid

• ChemBase ID: 169383
• Molecular Formular: C20H19N7O7
• Molecular Mass: 469.40756
• Monoisotopic Mass: 469.13459598
• SMILES: n1c(nc2c(c1=O)nc(c[nH]2)CN(c1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=O)N
• Canonical SMILES: O=CN(c1ccc(cc1)C(=O)N[C@H](C(=O)O)CCC(=O)O)Cc1c[nH]c2c(n1)c(=O)nc(n2)N
• InChI: InChI=1S/C20H19N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,7,9,13H,5-6,8H2,(H,24,31)(H,29,30)(H,33,34)(H3,21,22,25,26,32)/t13-/m0/s1
• InChIKey: UGWUWNVTCLDEOG-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{N-[(2-amino-4-oxo-4,8-dihydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: (2S)-2-[(4-{N-[(2-amino-4-oxo-8H-pteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
• Synonyms: N-[4-[[(2-Amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]formylamino]benzoyl]-L-glutamic Acid; 10-Formylpteroylglutamic Acid; N10-Formylfolic Acid; N-[p-[N-[(2-Amino-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamic Acid; 10-Formyl Folic Acid

Database IDs

• CAS Number: 134-05-4
• PubChem SID: 162263515
• PubChem CID: 3080544

CALCULATED PROPERTIES

• Molar Refractivity: 114.0589 cm^3
• Polarizability: 42.4835 Å^3
• Polar Surface Area: 216.21 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• Acid pKa: 3.1466541
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -5.573391
• LogD (pH = 7.4): -8.3714285
• Log P: -1.9306116

DETAILS

Toronto Research Chemicals - F700450

A Folic acid (F680300) derivative (or folate) found in daily dietary intake that is often used in cancer risk correlation studies.

REFERENCES

• Keszei, A.P. et al.: Cancer Epidimiol. Biomarker Prev., 18, 1785 (2009)
• Koning, E.J. et al.: Cancer, 95, 1421 (2009)