(2S)-2-[(4-{3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl}phenyl)formamido]pentanedioic acid

• ChemBase ID: 169349
• Molecular Formular: C20H23N7O6
• Molecular Mass: 457.43992
• Monoisotopic Mass: 457.17098149
• SMILES: [nH]1c(nc2c(c1=O)N1C(CN2)CN(C1)c1ccc(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)N1CC2N(C1)c1c(NC2)nc([nH]c1=O)N
• InChI: InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12?,13-/m0/s1
• InChIKey: QYNUQALWYRSVHF-ABLWVSNPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: N--L-glutamic acid
• Synonyms: N-[4-(3-Amino-1,2,5,6,6a,7-hexahydro-1-oxoimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-L-glutamic Acid; (+)-5,10-Methylene-5,6,7,8-tetrahydrofolic Acid; N5,N10-Methyl-enetetrahydrofolic Acid; N5,N10-Methylenetetrahydropteroylglutamic Acid; CoFactor; Folitixorin(Mixture of Diastereomers)

Database IDs

• CAS Number: 3432-99-3
• PubChem SID: 162263481
• PubChem CID: 108194

CALCULATED PROPERTIES

• Acid pKa: 2.9303067
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -4.428463
• LogD (pH = 7.4): -7.146236
• Log P: -2.0198555
• Molar Refractivity: 123.9566 cm^3
• Polarizability: 42.452656 Å^3
• Polar Surface Area: 189.69 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F680350

A stable folate lyophilized compound suitable for use in the treatment of cancer and other therapies.

REFERENCES

• Park, H., et al.: Science, 268, 1866 (1995)
• Banerjee, R., et al.: J. Biol. Chem., 282, 14916 (1995)
• Klar, T., et al.: J. Mol. Biol., 366, 954 (1995)