(3E)-4-{4-[2-(dimethylamino)ethoxy]phenyl}-3,4-diphenylbut-3-en-2-ol

• ChemBase ID: 171329
• Molecular Formular: C26H29NO2
• Molecular Mass: 387.51396
• Monoisotopic Mass: 387.21982917
• SMILES: c1c(ccc(c1)/C(=C(/C(O)C)\c1ccccc1)/c1ccccc1)OCCN(C)C
• Canonical SMILES: CN(CCOc1ccc(cc1)/C(=C(\c1ccccc1)/C(O)C)/c1ccccc1)C
• InChI: InChI=1S/C26H29NO2/c1-20(28)25(21-10-6-4-7-11-21)26(22-12-8-5-9-13-22)23-14-16-24(17-15-23)29-19-18-27(2)3/h4-17,20,28H,18-19H2,1-3H3/b26-25-
• InChIKey: BPHFBQJMFWCHGH-QPLCGJKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E)-4-{4-[2-(dimethylamino)ethoxy]phenyl}-3,4-diphenylbut-3-en-2-ol
• IUPAC Traditional name: α-hydroxytamoxifen
• Synonyms: (βE)-β-[[4-[2-(Dimethylamino)ethoxy]phenyl]phenylmethylene]-α-methyl-benzeneethanol; (E)-α-Hydroxy Tamoxifen

Database IDs

• CAS Number: 97151-02-5
• PubChem SID: 164227239
• PubChem CID: 3036580

CALCULATED PROPERTIES

• Acid pKa: 14.803913
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.977246
• LogD (pH = 7.4): 3.664228
• Log P: 5.042457
• Molar Refractivity: 130.0233 cm^3
• Polarizability: 47.05209 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 115-119°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H954700

A metabolite of the chemotherapeutic drug Tamoxifen (T006000). Exhibits a more potent estrogen agonist/antagonist activity than the parent drug. Also active as an intramembranous inhibitor of lipid peroxidation.

REFERENCES

• Kupfer, D., et al.: Cancer Res., 54, 3140 (1994)
• Custodio, J.B.A., et al.: Biochem. Pharmacol., 47, 1989 (1994)