(3S)-1-[3,4-dihydroxy-4,4-bis(3-methylthiophen-2-yl)butyl]piperidine-3-carboxylic acid

• ChemBase ID: 167884
• Molecular Formular: C20H27NO4S2
• Molecular Mass: 409.56268
• Monoisotopic Mass: 409.13815035
• SMILES: C(C(CCN1C[C@H](CCC1)C(=O)O)O)(c1c(ccs1)C)(c1c(ccs1)C)O
• Canonical SMILES: OC(=O)[C@H]1CCCN(C1)CCC(C(c1sccc1C)(c1sccc1C)O)O
• InChI: InChI=1S/C20H27NO4S2/c1-13-6-10-26-17(13)20(25,18-14(2)7-11-27-18)16(22)5-9-21-8-3-4-15(12-21)19(23)24/h6-7,10-11,15-16,22,25H,3-5,8-9,12H2,1-2H3,(H,23,24)/t15-,16?/m0/s1
• InChIKey: LRLPWDNQYQPWNA-VYRBHSGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-1-[3,4-dihydroxy-4,4-bis(3-methylthiophen-2-yl)butyl]piperidine-3-carboxylic acid
• IUPAC Traditional name: (3S)-1-[3,4-dihydroxy-4,4-bis(3-methylthiophen-2-yl)butyl]piperidine-3-carboxylic acid
• Synonyms: (R)-1-[4,4-Bis(3-methyl-2-thienyl)-3,4-dihydroxybutyl]-3-piperidinecarboxylic Acid; Dihydroxytiagabine; Tiagabine Impurity 1; Dihydroxy Tiagabine (Mixture of Diastereomers)

Database IDs

• PubChem SID: 162262017
• PubChem CID: 71316276

CALCULATED PROPERTIES

• Acid pKa: 3.8981323
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.57960534
• LogD (pH = 7.4): 0.56929654
• Log P: 0.5851541
• Molar Refractivity: 108.1844 cm^3
• Polarizability: 41.757927 Å^3
• Polar Surface Area: 81.0 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D455030

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

REFERENCES

• Hubert-Roux, M. et al.: Rap. Comm. Mass Spec., 26, 287 (2012)