(2S)-2-{[4-({[2-amino-5-(2H3)methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid

• ChemBase ID: 174340
• Molecular Formular: C20H25N7O6
• Molecular Mass: 459.4558
• Monoisotopic Mass: 459.18663156
• SMILES: n1c([nH]c2c(c1=O)N(C(CN2)CNc1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O)C)N
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NCC1CNc2c(N1C)c(=O)nc([nH]2)N
• InChI: InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m0/s1
• InChIKey: ZNOVTXRBGFNYRX-ABLWVSNPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[4-({[2-amino-5-(^2H₃)methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
• IUPAC Traditional name: (2S)-2-{[4-({[2-amino-5-(^2H₃)methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
• Synonyms: N-[4-[[(2-Amino-3,4,5,6,7,8-hexahydro-5-(methyl-d3)-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid; N-(Methyl-d3)tetrahydrofolate; N5-(Methyl-d3)tetrahydrofolate; N5-(Methyl-d3)tetrahydropteroylglutamate; Prefolic A-d3; 5-(Methyl-d3)tetrahydrofolic Acid (Mixture of Diastereomers)

Database IDs

• CAS Number: 1356019-97-0
• PubChem SID: 164230250
• PubChem CID: 46782314

CALCULATED PROPERTIES

• Acid pKa: 3.419046
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -5.4424167
• LogD (pH = 7.4): -8.077267
• Log P: -2.288805
• Molar Refractivity: 126.6813 cm^3
• Polarizability: 43.15752 Å^3
• Polar Surface Area: 198.48 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M330137

A labelled metabolite of Folic acid; inhibits photosensitization reactions and strand breaks in DNA; reduces total serum homocysteine level in orthotopic liver transplant recipients.

REFERENCES

• Fassbender, K., et al.: Lancet, 353, 1586 (1999)
• Pruthi, J., et al.: Liver Transpl., 7, 811 (1999)
• Wu, L., et al.: Clin. Chim. Acta, 322, 21 (1999)
• Eisen, H., et al.: N. Engl. J. Med., 349, 847 (1999)