1,5-dimethyl (2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate

• ChemBase ID: 176256
• Molecular Formular: C22H25N5O6
• Molecular Mass: 455.4638
• Monoisotopic Mass: 455.18048355
• SMILES: c1(nc(=O)c2c([nH]1)[nH]cc2CCc1ccc(cc1)C(=O)N[C@H](CCC(=O)OC)C(=O)OC)N
• Canonical SMILES: COC(=O)CC[C@H](C(=O)OC)NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)nc([nH]2)N
• InChI: InChI=1S/C22H25N5O6/c1-32-16(28)10-9-15(21(31)33-2)25-19(29)13-6-3-12(4-7-13)5-8-14-11-24-18-17(14)20(30)27-22(23)26-18/h3-4,6-7,11,15H,5,8-10H2,1-2H3,(H,25,29)(H4,23,24,26,27,30)/t15-/m1/s1
• InChIKey: WWYZIXUUERDREV-OAHLLOKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,5-dimethyl (2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate
• IUPAC Traditional name: 1,5-dimethyl (2R)-2-{[4-(2-{2-amino-4-oxo-1H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate
• Synonyms: N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic Acid 1,5-Dimethyl Ester; Pemetrexed Methyl Ester; N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic Acid 1,5-Dimethyl Diester; D-Pemetrexed Dimethyl Diester

Database IDs

• CAS Number: 155405-81-5
• PubChem SID: 164232166
• PubChem CID: 53235594

CALCULATED PROPERTIES

• Acid pKa: 9.184043
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 1.7797999
• LogD (pH = 7.4): 1.7731618
• Log P: 1.7799115
• Molar Refractivity: 118.9878 cm^3
• Polarizability: 44.54818 Å^3
• Polar Surface Area: 164.97 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Dimethylformamide; DMSO; Methanol
• Apperance: Brown Solid; Off-White Solid

DETAILS

Toronto Research Chemicals - P219535

Protected D-Pemetrexed (P219490).

Toronto Research Chemicals - P219525

Protected Pemetrexed.