(2R)-2-{[4-(2-{2-amino-4,6-dioxo-1H,4H,5H,6H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioic acid

• ChemBase ID: 172440
• Molecular Formular: C20H21N5O7
• Molecular Mass: 443.41004
• Monoisotopic Mass: 443.14409804
• SMILES: c1(ccc(cc1)C(=O)N[C@H](CCC(=O)O)C(=O)O)CCC1c2c(=O)nc([nH]c2NC1=O)N
• Canonical SMILES: OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)CCC1C(=O)Nc2c1c(=O)nc([nH]2)N
• InChI: InChI=1S/C20H21N5O7/c21-20-24-15-14(18(30)25-20)11(17(29)23-15)6-3-9-1-4-10(5-2-9)16(28)22-12(19(31)32)7-8-13(26)27/h1-2,4-5,11-12H,3,6-8H2,(H,22,28)(H,26,27)(H,31,32)(H4,21,23,24,25,29,30)/t11?,12-/m1/s1
• InChIKey: YVRHJHKPTURIID-PIJUOVFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[4-(2-{2-amino-4,6-dioxo-1H,4H,5H,6H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioic acid
• IUPAC Traditional name: (2R)-2-{[4-(2-{2-amino-4,6-dioxo-1H,5H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioic acid
• Synonyms: N-[4-[2-(2-Amino-4,5,6,7-tetrahydro-4,6-dioxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic Acid; LY 338979

Database IDs

• CAS Number: 193281-00-4
• PubChem SID: 164228350
• PubChem CID: 71749862

CALCULATED PROPERTIES

• Acid pKa: 3.3067083
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -4.335514
• LogD (pH = 7.4): -7.45897
• Log P: -0.86147743
• Molar Refractivity: 117.5236 cm^3
• Polarizability: 40.973755 Å^3
• Polar Surface Area: 200.28 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L486650

LY 338979 is a metabolite of the antifolate Pemetrexed (P219500).

REFERENCES

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