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

• ChemBase ID: 170447
• Molecular Formular: C25H27NO2
• Molecular Mass: 373.48738
• Monoisotopic Mass: 373.20417911
• SMILES: c1c(ccc(c1)/C(=C(\CC)/c1ccccc1)/c1ccc(cc1)O)OCCNC
• Canonical SMILES: CNCCOc1ccc(cc1)/C(=C(/c1ccccc1)\CC)/c1ccc(cc1)O
• InChI: InChI=1S/C25H27NO2/c1-3-24(19-7-5-4-6-8-19)25(20-9-13-22(27)14-10-20)21-11-15-23(16-12-21)28-18-17-26-2/h4-16,26-27H,3,17-18H2,1-2H3/b25-24+
• InChIKey: MHJBZVSGOZTKRH-OCOZRVBESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1E)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol
• IUPAC Traditional name: 4-[(1E)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol
• Synonyms: 4-[(1E)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol; E-Endoxifen; (E)-4-Hydroxy-N-desmethyl Tamoxifen

Database IDs

• CAS Number: 114828-90-9
• PubChem SID: 164226357
• PubChem CID: 3035980

CALCULATED PROPERTIES

• Acid pKa: 9.122582
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.4970224
• LogD (pH = 7.4): 3.6150854
• Log P: 4.9199395
• Molar Refractivity: 125.117 cm^3
• Polarizability: 45.190342 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 154-156°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H938495

A novel active metabolite of the anti-cancer drug Tamoxifen (T006000). It showed potent ER binding property, blocked estrogen stimulated growth of breast cancer cell and half maximal inhibition of estrogen responsive gene expression in ER pos. human breas

REFERENCES

• Furr, B., et al.: Pharmacol. Ther., 25, 127 (1984)
• Leonessa, F., et al.: Cancer Res., 54, 441 (1984)
• Stearns, V., et al.: Lancet, 360, 1851 (1984)
• Rae, J., et al.: Pharmacogenetics, 13, 501 (1984)