(3R)-3-(3-methanesulfonylphenyl)piperidine; 2,3-dihydroxybutanedioic acid

• ChemBase ID: 172596
• Molecular Formular: C16H23NO8S
• Molecular Mass: 389.42072
• Monoisotopic Mass: 389.1144377
• SMILES: c1(cccc(c1)[C@@H]1CNCCC1)S(=O)(=O)C.C(C(O)C(=O)O)(O)C(=O)O
• Canonical SMILES: CS(=O)(=O)c1cccc(c1)[C@H]1CCCNC1.OC(=O)C(C(C(=O)O)O)O
• InChI: InChI=1S/C12H17NO2S.C4H6O6/c1-16(14,15)12-6-2-4-10(8-12)11-5-3-7-13-9-11;5-1(3(7)8)2(6)4(9)10/h2,4,6,8,11,13H,3,5,7,9H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t11-;/m0./s1
• InChIKey: JUXRLGRCXHOPLH-MERQFXBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-(3-methanesulfonylphenyl)piperidine; 2,3-dihydroxybutanedioic acid
• IUPAC Traditional name: (.+-.)-tartaric acid; (3R)-3-(3-methanesulfonylphenyl)piperidine
• Synonyms: Despropyl (-)-OSU; Despropyl PNU 96391A; 3S-(-)-3-[3-(Methanesulfonyl)phenyl]piperidine Tartaric Acid Salt

Database IDs

• CAS Number: 504398-38-3
• PubChem SID: 164228506
• PubChem CID: 71433831

CALCULATED PROPERTIES

• Acid pKa: 19.69774
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.1968303
• LogD (pH = 7.4): -1.2301165
• Log P: 0.99657303
• Molar Refractivity: 65.4056 cm^3
• Polarizability: 26.229097 Å^3
• Polar Surface Area: 46.17 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Dimethylformamide
• Apperance: Yellow Gel

DETAILS

Toronto Research Chemicals - M258826

A metabolite of (-)-OSU (Cat. # O006162).

REFERENCES

• Drug Metabolism and Disposition 37: 937 (2009)