4-[(1Z)-1-{4-[2-(methylamino)ethoxy]phenyl}-1-phenylbut-1-en-2-yl]phenol

• ChemBase ID: 166473
• Molecular Formular: C25H27NO2
• Molecular Mass: 373.48738
• Monoisotopic Mass: 373.20417911
• SMILES: c1cc(ccc1)/C(=C(\CC)/c1ccc(cc1)O)/c1ccc(cc1)OCCNC
• Canonical SMILES: CNCCOc1ccc(cc1)/C(=C(\c1ccc(cc1)O)/CC)/c1ccccc1
• InChI: InChI=1S/C25H27NO2/c1-3-24(19-9-13-22(27)14-10-19)25(20-7-5-4-6-8-20)21-11-15-23(16-12-21)28-18-17-26-2/h4-16,26-27H,3,17-18H2,1-2H3
• InChIKey: KLPBCGLMGLFHNY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1Z)-1-{4-[2-(methylamino)ethoxy]phenyl}-1-phenylbut-1-en-2-yl]phenol; 4-(1-{4-[2-(methylamino)ethoxy]phenyl}-1-phenylbut-1-en-2-yl)phenol
• IUPAC Traditional name: 4-[(1Z)-1-{4-[2-(methylamino)ethoxy]phenyl}-1-phenylbut-1-en-2-yl]phenol; 4-(1-{4-[2-(methylamino)ethoxy]phenyl}-1-phenylbut-1-en-2-yl)phenol
• Synonyms: 4-[(1Z)-1-[[4-[2-(Methylamino)ethoxy]phenyl]phenylmethylene]propyl]phenol; (Z)-4-[1-[[4-[2-(Methylamino)ethoxy]phenyl]phenylmethylene]propyl]phenol; N-Desmethyl-4'-hydroxy Tamoxifen; 4-[(1E/Z)-1-[[4-[2-(Methylamino)ethoxy]phenyl]phenylmethylene]propyl]phenol; N-Desmethyl-4'-hydroxy Tamoxifen (E/Z Mixture)

Database IDs

• CAS Number: 170171-12-7
• PubChem SID: 162260606
• PubChem CID: 24873532

CALCULATED PROPERTIES

• Acid pKa: 9.145438
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.4964767
• LogD (pH = 7.4): 3.612217
• Log P: 4.9281197
• Molar Refractivity: 125.117 cm^3
• Polarizability: 45.19028 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Tan Solid; Yellow Solid
• Melting Point: 48-54°C; 58-66°C

Safety Information

• Storage Condition: -20°C Freezer; Amber Vial, -20°C Freezer

DETAILS

Toronto Research Chemicals - D292041

A metabolite of Tamoxifen (T006000).

Toronto Research Chemicals - D291865

A metabolite of the anti-cancer drug Tamoxifen (T006000).

REFERENCES

• Clarke, R., et al.: Pharmacol. Rev., 53, 25, (2001)
• Rae, J.M., et al.: Drug Metab. Dispos., 30, 525 (2001)
• Coller, J.K., et al.: Br. J. Clin. Pharmacol., 57, 105 (2004)
• Heiman, D., et al.: J. Med. Chem., 23, 994 (1980)
• Kier, L., et al.: Pharm. Res., 7, 801 (1980)