(3R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one

• ChemBase ID: 171844
• Molecular Formular: C11H16N2O2
• Molecular Mass: 208.25694
• Monoisotopic Mass: 208.12117776
• SMILES: [C@H]1(C(COC1=O)Cc1cncn1C)CC
• Canonical SMILES: CC[C@H]1C(=O)OCC1Cc1cncn1C
• InChI: InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8?,10-/m1/s1
• InChIKey: QCHFTSOMWOSFHM-LHIURRSHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one
• IUPAC Traditional name: (3R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one
• Synonyms: (3R,4R)-3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone; (3R-trans)-3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone; 3-Isopilocarpine; (+)-Isopilocarpine; β-Pilocarpine; Isopilocarpine

Database IDs

• CAS Number: 531-35-1
• PubChem SID: 164227754
• PubChem CID: 12311175

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.44190395
• LogD (pH = 7.4): 0.9023369
• Log P: 0.94975144
• Molar Refractivity: 56.5342 cm^3
• Polarizability: 21.845087 Å^3
• Polar Surface Area: 44.12 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I821970

An isomeric degradation product of Pilocarpine (P441500) with significantly lower binding affinity to muscarinic cholinergic receptors (~0.1 that of Pilocarpine).

REFERENCES

• Drake, M.V. et al.: J. Pharmac. Sci., 75, 278 (1986)
• Szepesi, G. et al.: Pharmazie, 38, 94 (1986)
• Bundgaard, H. et al.: Int. J. Pharmac., 10, 281 (1986)