2-methoxy-5-[(1S)-3-(methylamino)-1-(thiophen-2-yl)propoxy]naphthalen-1-ol

• ChemBase ID: 170747
• Molecular Formular: C19H21NO3S
• Molecular Mass: 343.43994
• Monoisotopic Mass: 343.12421454
• SMILES: c1(cccc2c1ccc(c2O)OC)O[C@H](c1sccc1)CCNC
• Canonical SMILES: CNCC[C@@H](c1cccs1)Oc1cccc2c1ccc(c2O)OC
• InChI: InChI=1S/C19H21NO3S/c1-20-11-10-16(18-7-4-12-24-18)23-15-6-3-5-14-13(15)8-9-17(22-2)19(14)21/h3-9,12,16,20-21H,10-11H2,1-2H3/t16-/m0/s1
• InChIKey: MHWRJCBZOCBFBD-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methoxy-5-[(1S)-3-(methylamino)-1-(thiophen-2-yl)propoxy]naphthalen-1-ol
• IUPAC Traditional name: 2-methoxy-5-[(1S)-3-(methylamino)-1-(thiophen-2-yl)propoxy]naphthalen-1-ol
• Synonyms: 2-Methoxy-5-[(1S)-3-(methylamino)-1-(2-thienyl)propoxy]-1-naphthalenol; 5-Hydroxy-6-methoxy Duloxetine

Database IDs

• CAS Number: 741693-79-8
• PubChem SID: 164226657
• PubChem CID: 29981679

CALCULATED PROPERTIES

• Acid pKa: 9.286793
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.5450314
• LogD (pH = 7.4): 1.5231776
• Log P: 2.9990873
• Molar Refractivity: 96.178 cm^3
• Polarizability: 38.774227 Å^3
• Polar Surface Area: 50.72 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H946300

A metabolite of Duloxetine.

REFERENCES

• Cheng, Y., et al.: Biochem. Pharmacol., 22, 3099 (1973)
• Detke, M., et al.: J. Clin. Psy., 63, 308 (1973)
• Bymaster, F., et al.: Bioorg. Med. Chem. Lett., 13, 4477 (1973)
• Lantz, R., et al.: Drug Dispos. Metab., 31, 1142 (1973)