5-benzoyl-N-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2,3-dihydro(2,2,3,3-2H4)-1H-pyrrolizine-1-carboxamide

• ChemBase ID: 172119
• Molecular Formular: C19H22N2O5
• Molecular Mass: 358.38838
• Monoisotopic Mass: 358.15287181
• SMILES: c1cc2n(c1C(=O)c1ccccc1)CCC2C(=O)NC(CO)(CO)CO
• Canonical SMILES: OCC(NC(=O)C1CCn2c1ccc2C(=O)c1ccccc1)(CO)CO
• InChI: InChI=1S/C19H22N2O5/c22-10-19(11-23,12-24)20-18(26)14-8-9-21-15(14)6-7-16(21)17(25)13-4-2-1-3-5-13/h1-7,14,22-24H,8-12H2,(H,20,26)
• InChIKey: QYIXDZZHVVTARJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-benzoyl-N-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2,3-dihydro(2,2,3,3-^2H₄)-1H-pyrrolizine-1-carboxamide
• IUPAC Traditional name: 5-benzoyl-N-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl](2,2,3,3-^2H₄)-1H-pyrrolizine-1-carboxamide
• Synonyms: (±)-5-Benzoyl-2,3-dihydro-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]-1H-pyrrolizine-1-carboxamide-d4; Ketoroloc Impurity E-d4; rac Ketoroloc Tris Amide Impurity-d4

Database IDs

• PubChem SID: 164228029
• PubChem CID: 71749700

CALCULATED PROPERTIES

• Acid pKa: 12.091577
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -0.38667393
• LogD (pH = 7.4): -0.38668168
• Log P: -0.38667384
• Molar Refractivity: 95.3501 cm^3
• Polarizability: 36.79491 Å^3
• Polar Surface Area: 111.79 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K235642

A labelled impurity of Ketorolac (K235650).

REFERENCES

• Brandl, M. et al.: J. Pharmac. Sci., 84, 1151 (1995)