4-[(1Z)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenyl(2H5)but-1-en-1-yl]phenol

• ChemBase ID: 166508
• Molecular Formular: C25H27NO2
• Molecular Mass: 373.48738
• Monoisotopic Mass: 373.20417911
• SMILES: c1cc(ccc1O)/C(=C(\CC)/c1ccccc1)/c1ccc(cc1)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-IZHYLOQSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1Z)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenyl(^2H₅)but-1-en-1-yl]phenol
• IUPAC Traditional name: 4-[(1Z)-1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenyl(^2H₅)but-1-en-1-yl]phenol
• Synonyms: 4-[1-[4-[2-(Methylamino)ethoxy]phenyl]-2-phenyl-1-butenyl-d5]phenol; (E/Z-Endoxifen-d5; 4OHNDtam-d5; N-Desmethyl-4-hydroxy Tamoxifen-d5 (1:1 E/Z Mixture)

Database IDs

• PubChem SID: 162260641
• PubChem CID: 45038886

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: 45.191387 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO; Methanol
• Apperance: Off-White to Light Pink Solid
• Melting Point: 74-78°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D292044

A novel active labelled 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. hu

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)