4-(2-{2-amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)benzoic acid

• ChemBase ID: 160016
• Molecular Formular: C15H14N4O3
• Molecular Mass: 298.29666
• Monoisotopic Mass: 298.10659033
• SMILES: c1([nH]c(=O)c2c(n1)[nH]cc2CCc1ccc(cc1)C(=O)O)N
• Canonical SMILES: Nc1nc2[nH]cc(c2c(=O)[nH]1)CCc1ccc(cc1)C(=O)O
• InChI: InChI=1S/C15H14N4O3/c16-15-18-12-11(13(20)19-15)10(7-17-12)6-3-8-1-4-9(5-2-8)14(21)22/h1-2,4-5,7H,3,6H2,(H,21,22)(H4,16,17,18,19,20)
• InChIKey: AIZPFZIKHIJCQX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-{2-amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)benzoic acid
• IUPAC Traditional name: 4-(2-{2-amino-4-oxo-3H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)benzoic acid
• Synonyms: 4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid; 4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic Acid

Database IDs

• CAS Number: 137281-39-1
• PubChem SID: 162254151
• PubChem CID: 9796279

CALCULATED PROPERTIES

• Acid pKa: 4.482305
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.5989975
• LogD (pH = 7.4): -1.1191854
• Log P: 1.3583903
• Molar Refractivity: 81.7952 cm^3
• Polarizability: 29.342272 Å^3
• Polar Surface Area: 120.57 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: Pale Pink Solid
• Melting Point: >270°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A604905

Pemetrexed intermediate.

REFERENCES

• Taylor, E., et al.: J. Med. Chem., 35, 4450 (1992)
• Shih, C., et al.: Cancer Res., 57, 1116 (1992)
• Yan, X., et al.: J. Mol. Biol., 266, 1043 (1997)