(2Z)-but-2-enedioic acid; 1-(3-hydroxy-4-methylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one

• ChemBase ID: 171382
• Molecular Formular: C20H27NO6
• Molecular Mass: 377.43148
• Monoisotopic Mass: 377.18383759
• SMILES: c1c(c(ccc1C(=O)C(CN1CCCCC1)C)C)O.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: CC(C(=O)c1ccc(c(c1)O)C)CN1CCCCC1.OC(=O)/C=C\C(=O)O
• InChI: InChI=1S/C16H23NO2.C4H4O4/c1-12-6-7-14(10-15(12)18)16(19)13(2)11-17-8-4-3-5-9-17;5-3(6)1-2-4(7)8/h6-7,10,13,18H,3-5,8-9,11H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChIKey: LBIPWJFYYZEVQC-BTJKTKAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; 1-(3-hydroxy-4-methylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one
• IUPAC Traditional name: 1-(3-hydroxy-4-methylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one; maleic acid
• Synonyms: 1-(3-Hydroxy-4-methylphenyl)-2-methyl-3-(1-piperidinyl)-1-propanone (2Z)-2-Butenedioate; 3-Hydroxy Tolperisone Maleate

Database IDs

• CAS Number: 283585-02-4
• PubChem SID: 164227292
• PubChem CID: 71749380

CALCULATED PROPERTIES

• Acid pKa: 9.426506
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.25687948
• LogD (pH = 7.4): 1.9620074
• Log P: 2.8925622
• Molar Refractivity: 78.3278 cm^3
• Polarizability: 30.124008 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H969880

A metabolite of Tolperisone (T535475).

REFERENCES

• Shiozawa, A., et al.: Eur. J. Med. Chem. Chim. Ther., 30, 85 (1995)