(3S)-1-[4,4-bis(3-methylthiophen-2-yl)-3-oxobutyl]piperidine-3-carboxylic acid; 4-methylbenzene-1-sulfonic acid

• ChemBase ID: 172124
• Molecular Formular: C27H33NO6S3
• Molecular Mass: 563.74902
• Monoisotopic Mass: 563.14700078
• SMILES: C(C(=O)CCN1C[C@H](CCC1)C(=O)O)(c1c(ccs1)C)c1c(ccs1)C.c1cc(ccc1C)S(=O)(=O)O
• Canonical SMILES: O=C(C(c1sccc1C)c1sccc1C)CCN1CCC[C@@H](C1)C(=O)O.Cc1ccc(cc1)S(=O)(=O)O
• InChI: InChI=1S/C20H25NO3S2.C7H8O3S/c1-13-6-10-25-18(13)17(19-14(2)7-11-26-19)16(22)5-9-21-8-3-4-15(12-21)20(23)24;1-6-2-4-7(5-3-6)11(8,9)10/h6-7,10-11,15,17H,3-5,8-9,12H2,1-2H3,(H,23,24);2-5H,1H3,(H,8,9,10)/t15-;/m0./s1
• InChIKey: PXDIWSZORHMNBU-RSAXXLAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-1-[4,4-bis(3-methylthiophen-2-yl)-3-oxobutyl]piperidine-3-carboxylic acid; 4-methylbenzene-1-sulfonic acid
• IUPAC Traditional name: (3S)-1-[4,4-bis(3-methylthiophen-2-yl)-3-oxobutyl]piperidine-3-carboxylic acid; toluenesulfonic acid
• Synonyms: (R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-oxobutyl]-3-piperidinecarboxylic Acid 4-Methylbenzenesulfonate; Ketotiagabine Tosylate; Tiagabine Impurity 2; Oxotiagabine Tosylate; Keto Tiagabine Tosylate

Database IDs

• CAS Number: 161014-56-8
• PubChem SID: 164228034
• PubChem CID: 71749701

CALCULATED PROPERTIES

• Acid pKa: 3.9980218
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.1169772
• LogD (pH = 7.4): 2.095068
• Log P: 2.123709
• Molar Refractivity: 105.8047 cm^3
• Polarizability: 40.565353 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - K315050

Keto Tiagabine Tosylate is an impurity of the GABA uptake inhibitor Tiagabine (T436400).

REFERENCES

• Callen, G. et al.: Heterocycles, 39, 293 (1994)