1,5-dimethyl (2S)-2-[(4-{[(2,4-diamino-7-cyanopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioate

• ChemBase ID: 165103
• Molecular Formular: C23H25N9O5
• Molecular Mass: 507.5019
• Monoisotopic Mass: 507.19786495
• SMILES: c1c(ccc(c1)N(Cc1nc2c(nc1C#N)nc(nc2N)N)C)C(=O)N[C@@H](CCC(=O)OC)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H](NC(=O)c1ccc(cc1)N(Cc1nc2c(N)nc(nc2nc1C#N)N)C)CCC(=O)OC
• InChI: InChI=1S/C23H25N9O5/c1-32(11-16-15(10-24)28-20-18(27-16)19(25)30-23(26)31-20)13-6-4-12(5-7-13)21(34)29-14(22(35)37-3)8-9-17(33)36-2/h4-7,14H,8-9,11H2,1-3H3,(H,29,34)(H4,25,26,28,30,31)/t14-/m0/s1
• InChIKey: IELAPFQSSXNBBQ-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,5-dimethyl (2S)-2-[(4-{[(2,4-diamino-7-cyanopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioate
• IUPAC Traditional name: 1,5-dimethyl (2S)-2-[(4-{[(2,4-diamino-7-cyanopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioate
• Synonyms: N-[4-[[(2,4-Diamino-7-cyano-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic Acid Dimethyl Ester; 7-Cyanomethotrexate Dimethyl Ester

Database IDs

• CAS Number: 112163-39-0
• PubChem SID: 162259236
• PubChem CID: 13889753

CALCULATED PROPERTIES

• Acid pKa: 15.480753
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): 0.5315357
• LogD (pH = 7.4): 0.53160006
• Log P: 0.5316009
• Molar Refractivity: 134.0986 cm^3
• Polarizability: 49.52475 Å^3
• Polar Surface Area: 212.33 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Ethanol; Methanol
• Apperance: Red-Orange Solid

DETAILS

Toronto Research Chemicals - C981820

An intermediate in the production of Methotrexate metabolites

REFERENCES

• Dawson, M., et al.: J. Pharm. Sci., 76, 635 (1987)