(2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](2H3)methylamino}phenyl)formamido]pentanedioic acid

• ChemBase ID: 172860
• Molecular Formular: C20H22N8O5
• Molecular Mass: 454.43928
• Monoisotopic Mass: 454.17131584
• SMILES: n1c(nc2c(c1N)nc(cn2)CN(c1ccc(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)N(Cc1cnc2c(n1)c(N)nc(n2)N)C
• InChI: InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1
• InChIKey: FBOZXECLQNJBKD-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](^2H₃)methylamino}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: (2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](^2H₃)methylamino}phenyl)formamido]pentanedioic acid
• Synonyms: N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino-d3]benzoyl]-L-glutamic Acid; (+)-Amethopterin; 4-Amino-N10-methylpteroylglutamic Acid-d3; 4-Amino-N10-methylfolic Acid-d3; Antifolan-d3; Emtexate-d3; Ledertrexate-d3; MTX-d3; L-Metatrexan-d3; Methylaminopterin-d3; Mexate-d3; NSC 740; R 9985-d3; Rheumatrex-d3; Trexall-d3; Methotrexate-d3

Database IDs

• PubChem SID: 164228770
• PubChem CID: 10895754

CALCULATED PROPERTIES

• Acid pKa: 3.2608879
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -3.640823
• LogD (pH = 7.4): -6.5636883
• Log P: -0.23654379
• Molar Refractivity: 119.2108 cm^3
• Polarizability: 43.52216 Å^3
• Polar Surface Area: 210.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M260677

Labelled Methotrexate (M260675). A Folic acid antagonist. Used as a antineoplastic and antirheumatic.

REFERENCES

• Freeman, M.V., J. Pharmacol. Exp. Ther., 122, 154 (1958)
• Weinblass, M.E., et al.: N. Engl. J. Med., 312, 818 (1958)