(5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-ynoic acid

• ChemBase ID: 163794
• Molecular Formular: C21H23NO2
• Molecular Mass: 321.41282
• Monoisotopic Mass: 321.17287898
• SMILES: c12c(cccc1CN(C/C=C/C#CC(C)(C)C(=O)O)C)cccc2
• Canonical SMILES: CN(Cc1cccc2c1cccc2)C/C=C/C#CC(C(=O)O)(C)C
• InChI: InChI=1S/C21H23NO2/c1-21(2,20(23)24)14-7-4-8-15-22(3)16-18-12-9-11-17-10-5-6-13-19(17)18/h4-6,8-13H,15-16H2,1-3H3,(H,23,24)/b8-4+
• InChIKey: DSPCPJFHUUUMEV-XBXARRHUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-ynoic acid
• IUPAC Traditional name: (5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-ynoic acid
• Synonyms: (5E)-2,2-Dimethyl-7-[methyl(1-naphthalenylmethyl)amino]-5-hepten-3-ynoic Acid; Carboxybutylterbinafine; E-Carboxyterbinafine; Carboxy Terbinafine

Database IDs

• CAS Number: 99473-14-0
• PubChem SID: 162257929
• PubChem CID: 6443234

CALCULATED PROPERTIES

• Acid pKa: 3.9574041
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.9804511
• LogD (pH = 7.4): 1.9803537
• Log P: 1.9870915
• Molar Refractivity: 99.7924 cm^3
• Polarizability: 38.85173 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMF; Ethanol; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 118-120°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C182600

A metabolite of Terbinafine, an orally active, antimycotic allylamine related to naftifine.

REFERENCES

• Humbert, H., et al.: Pharam. Drug Dispos., 19, 417 (1998)
• Vickers, A., et al.: Drug Metab. Dispos., 27, 1029 (1998)
• Iverson, S., et al.: Chem. Res. Toxicol., 14, 175 (1998)