sodium (2R,3R)-2-ethyl-4-hydroxy-3-{[1-(2H3)methyl-1H-imidazol-5-yl]methyl}butanoate

• ChemBase ID: 171612
• Molecular Formular: C11H17N2NaO3
• Molecular Mass: 248.25405
• Monoisotopic Mass: 248.1136867
• SMILES: n1cc(n(c1)C)C[C@H]([C@@H](CC)C(=O)[O-])CO.[Na+]
• Canonical SMILES: OC[C@@H]([C@H](C(=O)[O-])CC)Cc1cncn1C.[Na+]
• InChI: InChI=1S/C11H18N2O3.Na/c1-3-10(11(15)16)8(6-14)4-9-5-12-7-13(9)2;/h5,7-8,10,14H,3-4,6H2,1-2H3,(H,15,16);/q;+1/p-1/t8-,10+;/m0./s1
• InChIKey: YGXGGGNCVNXKBE-KXNXZCPBSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,3R)-2-ethyl-4-hydroxy-3-{[1-(^2H₃)methyl-1H-imidazol-5-yl]methyl}butanoate
• IUPAC Traditional name: sodium (2R,3R)-2-ethyl-4-hydroxy-3-{[3-(^2H₃)methylimidazol-4-yl]methyl}butanoate
• Synonyms: [R-(R*,R*)]-α-Ethyl-β-(hydroxymethyl)-1-methyl-1H-imidazole-5-butanoic Acid-d3 Monosodium Salt; Isopilocarpinate-d3 Sodium Salt; Isopilocarpinic Acid-d3 Sodium Salt; (αR,βR)-α-Ethyl-β-(hydroxymethyl)-1-methyl-1H-imidazole-5-butanoic Acid-d3 Sodium Salt; 1,2-Seco-3-isopilocarpin-2-oic Acid-d3 Sodium Salt; Isopilocarpic Acid-d3 Sodium Salt

Database IDs

• PubChem SID: 164227522
• PubChem CID: 71749485

CALCULATED PROPERTIES

• Acid pKa: 4.339911
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.53404164
• LogD (pH = 7.4): -1.3701233
• Log P: -0.4824863
• Molar Refractivity: 70.8635 cm^3
• Polarizability: 22.936396 Å^3
• Polar Surface Area: 78.18 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I821962

Labelled Isopilocarpic Acid. Isopilocarpic Acid is a degradation product of Pilocarpine (P441500).

REFERENCES

• Szepesi, G. et al.: Pharmazie, 38, 94 (1983)
• Bundgaard, H. et al.: Int. J. Pharmac., 10, 281 (1983)