5-(4-hydroxybenzoyl)-2,3-dihydro(2,2,3,3-2H4)-1H-pyrrolizine-1-carboxylic acid

• ChemBase ID: 170682
• Molecular Formular: C15H13NO4
• Molecular Mass: 271.26802
• Monoisotopic Mass: 271.0844579
• SMILES: C1CC(c2n1c(cc2)C(=O)c1ccc(cc1)O)C(=O)O
• Canonical SMILES: OC(=O)C1CCn2c1ccc2C(=O)c1ccc(cc1)O
• InChI: InChI=1S/C15H13NO4/c17-10-3-1-9(2-4-10)14(18)13-6-5-12-11(15(19)20)7-8-16(12)13/h1-6,11,17H,7-8H2,(H,19,20)
• InChIKey: PIQMOWBWPFGZMW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(4-hydroxybenzoyl)-2,3-dihydro(2,2,3,3-^2H₄)-1H-pyrrolizine-1-carboxylic acid
• IUPAC Traditional name: 5-(4-hydroxybenzoyl)(2,2,3,3-^2H₄)-1H-pyrrolizine-1-carboxylic acid
• Synonyms: 2,3-Dihydro-5-(4-hydroxybenzoyl)-1H-pyrrolizine-1-carboxylic Acid-d4; (+/-)-p-Hydroxyketorolac-d4; p-Hydroxyketorolac-d4; 4-Hydroxy Ketorolac-d4

Database IDs

• PubChem SID: 164226592
• PubChem CID: 71749082

CALCULATED PROPERTIES

• Acid pKa: 3.677203
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.15675958
• LogD (pH = 7.4): -1.4839238
• Log P: 1.9797976
• Molar Refractivity: 72.1754 cm^3
• Polarizability: 27.465137 Å^3
• Polar Surface Area: 79.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H943652

A labelled hydroxylated metabolite of Ketorolac in plasma.

REFERENCES

• Mroszczak, E., et al.: Drug Metab. Dispos., 15, 618 (1987)
• Gillis, J., et al.: Drugs, 53, 139 (1987)