(2R,3R,4R,5S,6R)-6-(5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carbonyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 172114
• Molecular Formular: C21H21NO9
• Molecular Mass: 431.39274
• Monoisotopic Mass: 431.12163126
• SMILES: c12n(c(cc1)C(=O)c1ccccc1)CCC2C(=O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O
• Canonical SMILES: O=C(C1CCn2c1ccc2C(=O)c1ccccc1)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C21H21NO9/c23-14(10-4-2-1-3-5-10)13-7-6-12-11(8-9-22(12)13)20(29)31-21-17(26)15(24)16(25)18(30-21)19(27)28/h1-7,11,15-18,21,24-26H,8-9H2,(H,27,28)/t11?,15-,16-,17+,18-,21-/m1/s1
• InChIKey: OAKSFFKSMVSYJD-JRVQSNPHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-(5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carbonyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-(5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carbonyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylate] β-D-Glucopyranuronic Acid; rac Ketorolac Glucuronide; rac Ketorolac Acyl-β-D-glucuronide(Mixture of Diastereomers)

Database IDs

• PubChem SID: 164228024
• PubChem CID: 71749698

CALCULATED PROPERTIES

• Acid pKa: 3.2477643
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.8967367
• LogD (pH = 7.4): -3.1010888
• Log P: 0.3355694
• Molar Refractivity: 102.4931 cm^3
• Polarizability: 40.675877 Å^3
• Polar Surface Area: 155.52 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K235610

A metabolite of Ketorolac.

REFERENCES

• Mroszczak, E., et al.: Drug Metab. Dispos., 15, 618 (1987)
• Brocks, D., et al.: Clin. Pharmacokinet., 23, 415 (1987)
• Vakily, M., et al.: Pharm. Res., 12, 1652 (1987)
• Gillis, J., et al.: Drugs, 53, 139 (1987)