(2R)-2-[(4-{[(2-amino-4-oxo-4,8-dihydropteridin-7-yl)methyl]amino}phenyl)formamido]pentanedioic acid

• ChemBase ID: 171800
• Molecular Formular: C19H19N7O6
• Molecular Mass: 441.39746
• Monoisotopic Mass: 441.13968136
• SMILES: n1c(nc2c(c1=O)ncc([nH]2)CNc1ccc(cc1)C(=O)N[C@H](CCC(=O)O)C(=O)O)N
• Canonical SMILES: OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)NCc1cnc2c([nH]1)nc(nc2=O)N
• InChI: InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)22-8-11(23-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,23,25,26,30)/t12-/m1/s1
• InChIKey: AGSJDPWOEUMTCN-GFCCVEGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(4-{[(2-amino-4-oxo-4,8-dihydropteridin-7-yl)methyl]amino}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: (2R)-2-[(4-{[(2-amino-4-oxo-8H-pteridin-7-yl)methyl]amino}phenyl)formamido]pentanedioic acid
• Synonyms: N-[4-[[(2-Amino-1,4-dihydro-4-oxo-7-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid; N-[p-[[(2-Amino-4-hydroxy-7-pteridyl)methyl]amino]benzoyl]glutamic Acid; Isofolic Acid (EP-designation)DISCONTINUED

Database IDs

• CAS Number: 47707-78-8
• PubChem SID: 164227710
• PubChem CID: 71749561

CALCULATED PROPERTIES

• Acid pKa: 3.3906603
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -4.80148
• LogD (pH = 7.4): -7.805224
• Log P: -1.5824038
• Molar Refractivity: 110.7643 cm^3
• Polarizability: 40.525208 Å^3
• Polar Surface Area: 207.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I817500

The 7-Isomer of Pteroylglutamic acid (Folic acid) as potential PET radiopharmaceuticals.

REFERENCES

• Leamon, C., et al.: J. Biochem., 291, 855 (1993)
• Leamon, C., et al.: Bioconjugate Chem., 13, 1200 (1993)
• Mathias, C., et al.: Nucl. Med. Biol., 30, 725 (1993)