(2R)-2-({4-[3-(2,6-diamino-4-oxo-1,4-dihydropyrimidin-5-yl)-3-oxopropyl]phenyl}formamido)pentanedioic acid

• ChemBase ID: 172441
• Molecular Formular: C19H21N5O7
• Molecular Mass: 431.39934
• Monoisotopic Mass: 431.14409804
• SMILES: c1(ccc(cc1)C(=O)N[C@H](CCC(=O)O)C(=O)O)CCC(=O)c1c(=O)nc([nH]c1N)N
• Canonical SMILES: OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)CCC(=O)c1c(N)[nH]c(nc1=O)N
• InChI: InChI=1S/C19H21N5O7/c20-15-14(17(29)24-19(21)23-15)12(25)7-3-9-1-4-10(5-2-9)16(28)22-11(18(30)31)6-8-13(26)27/h1-2,4-5,11H,3,6-8H2,(H,22,28)(H,26,27)(H,30,31)(H5,20,21,23,24,29)/t11-/m1/s1
• InChIKey: GQMLDZYRTDSOMZ-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-({4-[3-(2,6-diamino-4-oxo-1,4-dihydropyrimidin-5-yl)-3-oxopropyl]phenyl}formamido)pentanedioic acid
• IUPAC Traditional name: (2R)-2-({4-[3-(2,4-diamino-6-oxo-3H-pyrimidin-5-yl)-3-oxopropyl]phenyl}formamido)pentanedioic acid
• Synonyms: N-[4-[3-(2,6-Diamino-1,4-dihydro-4-oxo-5-pyrimidinyl)-3-oxopropyl]benzoyl]-L-glutamic Acid; LY 368962

Database IDs

• CAS Number: 193281-05-9
• PubChem SID: 164228351
• PubChem CID: 71749863

CALCULATED PROPERTIES

• Acid pKa: 3.3018012
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -4.290124
• LogD (pH = 7.4): -7.8462844
• Log P: -0.6639752
• Molar Refractivity: 115.1768 cm^3
• Polarizability: 39.85817 Å^3
• Polar Surface Area: 214.27 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L486700

LY 368962 is a metabolite of the antifolate Pemetrexed (P219500).

REFERENCES

• Woodland, J.M. et al.: Drug Metab. Dispos., 25, 693 (1997)