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

• ChemBase ID: 154611
• Molecular Formular: C25H30ClNO3
• Molecular Mass: 427.9636
• Monoisotopic Mass: 427.19142151
• SMILES: CC/C(=C(/c1ccc(cc1)O)\c1ccc(cc1)OCCNC)/c1ccccc1.O.Cl
• Canonical SMILES: CNCCOc1ccc(cc1)/C(=C(/c1ccccc1)\CC)/c1ccc(cc1)O.O.Cl
• InChI: InChI=1S/C25H27NO2.ClH.H2O/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;1H;1H2
• InChIKey: BISAMGUAXFFKDX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl)phenol hydrate hydrochloride
• IUPAC Traditional name: 4-(1-{4-[2-(methylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl)phenol hydrate hydrochloride
• Synonyms: (E/Z)-4-Hydroxy-N-desmethyltamoxifen hydrochloride hydrate; (E/Z)-4-[1-[4-[2-(Methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol hydrochloride hydrate (1:1 E/Z mixture); (E/Z)-4OHNDtam hydrochloride hydrate; (E/Z)-Endoxifen hydrochloride hydrate; (E/Z)-Endoxifen Hydrochloride Hydrate

Database IDs

• MDL Number: MFCD16875406
• PubChem SID: 162248749
• PubChem CID: 71311909

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: DMSO: >10 mg/mL
• Apperance: white to beige solid

Safety Information

• Storage Condition: desiccated
• German water hazard class: nwg
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C25H27NO2 · HCl · xH2O

DETAILS

Sigma Aldrich - E8284

Biochem/physiol Actions
(E/Z)-Endoxifen hydrochloride ((E/Z)-4-Hydroxy-N-desmethyltamoxifen hydrochloride) is a tamoxifen metabolite and potent Selective Estrogen Response Modifier (SERM). It is equipotent to 4-hydroxytamoxifen with respect to estrogen receptor binding and inhibition of 17-estradiol (E2)-induced cell proliferation. It is primarily catalyzed by cytochrome P450 2D6 (CYP2D6). Mutations in CYP2D6 may prevent response to tamoxifen by preventing formation of endoxifen. The gene expression patterns of five genes have been validated to be differentially regulated by endoxifen and 4-OH-Tamoxifen. Endoxifen and 4-OH-Tam have similar effects on global gene expression patterns in MCF-7 cells and the majority of the affected genes are estrogen-regulated genes.