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

• ChemBase ID: 174339
• Molecular Formular: C20H25CaN7O6
• Molecular Mass: 499.5338
• Monoisotopic Mass: 499.14922254
• SMILES: n1c([nH]c2c(c1=O)N(C(CN2)CNc1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O)C)N.[Ca]
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NCC1CNc2c(N1C)c(=O)nc([nH]2)N.[Ca]
• InChI: InChI=1S/C20H25N7O6.Ca/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: BGJXXVMOQCHQBO-ZEDZUCNESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid calcium
• IUPAC Traditional name: (2S)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid calcium
• Synonyms: N-[4-[[(2-Amino-3,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid Calcium Trihydrate; N-Methyltetrahydrofolate Calcium Trihydrate; N5-Methyltetrahydrofolate Calcium Trihydrate; N5-MethyltetrahydropteroylglutamateCalcium Trihydrate; Prefolic A; Metafolin; 5-Methyltetrahydrofolic Acid Calcium Salt Trihydrate(Also See: L375720)

Database IDs

• PubChem SID: 164230249
• PubChem CID: 57369558

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 Solid
• Melting Point: >300°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - M330135

A 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)