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

• ChemBase ID: 166405
• Molecular Formular: C20H21NO2
• Molecular Mass: 307.38624
• Monoisotopic Mass: 307.15722892
• SMILES: c12c(cccc1CNC/C=C/C#CC(C)(C)C(=O)O)cccc2
• Canonical SMILES: OC(=O)C(C#C/C=C/CNCc1cccc2c1cccc2)(C)C
• InChI: InChI=1S/C20H21NO2/c1-20(2,19(22)23)13-6-3-7-14-21-15-17-11-8-10-16-9-4-5-12-18(16)17/h3-5,7-12,21H,14-15H2,1-2H3,(H,22,23)/b7-3+
• InChIKey: HLMXKUJHRUTHIL-XVNBXDOJSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 99473-15-1
• PubChem SID: 162260538
• PubChem CID: 6443235

CALCULATED PROPERTIES

• Acid pKa: 3.8834405
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.8564837
• LogD (pH = 7.4): 1.8599703
• Log P: 1.8628465
• Molar Refractivity: 94.4977 cm^3
• Polarizability: 37.004944 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Ethanol; Methanol
• Apperance: Yellow Solid
• Melting Point: 147-150°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D291405

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

REFERENCES

• Petranyi, G., et al.: Science, 224, 1239 (1984)
• Petranyi, G., et al.: Antimicrob. Agents Chemother., 31, 1365 (1984)
• Humbert, H., et al.: Biopharm. Drug Dispos., 16, 685 (1984)
• Nejjam, F., et al.: Br. J. Dermatol.,132, 98 (1984)