4-{1-Chloro-2-[4-(2-diethylamino-ethoxy)-phenyl]-2-phenyl-vinyl}-phenol

ID: ALA291809

Cas Number: 117095-64-4

PubChem CID: 3081118

Max Phase: Preclinical

Molecular Formula: C26H28ClNO2

Molecular Weight: 421.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCOc1ccc(/C(=C(/Cl)c2ccc(O)cc2)c2ccccc2)cc1

Standard InChI:  InChI=1S/C26H28ClNO2/c1-3-28(4-2)18-19-30-24-16-12-21(13-17-24)25(20-8-6-5-7-9-20)26(27)22-10-14-23(29)15-11-22/h5-17,29H,3-4,18-19H2,1-2H3/b26-25+

Standard InChI Key:  NXNAMKPCKKKOHX-OCEACIFDSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    6.1167   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -3.6167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1917   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750    2.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1917   -0.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -0.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6042   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -0.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -0.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -0.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6125   -0.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750    0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042    2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625    2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167    1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750    3.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4500   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -5.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -5.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  1  1  0
  6  2  1  0
  7  3  1  0
  8  3  2  0
  9  4  1  0
 10  4  2  0
 11 21  1  0
 12 14  2  0
 13 17  2  0
 14 10  1  0
 15  9  2  0
 16  7  2  0
 17  8  1  0
 18 13  1  0
 19 12  1  0
 20 18  1  0
 21 20  1  0
 22  5  1  0
 23  5  2  0
 24 11  1  0
 25 11  1  0
 26 24  1  0
 27 25  1  0
 28 23  1  0
 29 22  2  0
 30 28  2  0
 16 13  1  0
 29 30  1  0
 15 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA291809

   1-(Phenyl)-1-(4-(2-(diethylamino)-ethoxy)phenyl)-2-(4-hydroxyphenyl)-2-chloroethane

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 421.97

Molecular Weight (Monoisotopic): 421.1809

AlogP: 6.27

#Rotatable Bonds: 9

Polar Surface Area: 32.70

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.56

CX Basic pKa: 9.39

CX LogP: 5.25

CX LogD: 4.32

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.41

Np Likeness Score: -0.48

References

1. Ruenitz PC, Arrendale RF, Schmidt WF, Thompson CB, Nanavati NT..  (1989)  Phenolic metabolites of clomiphene: [(E,Z)-2-[4-(1,2-diphenyl-2-chlorovinyl)phenoxy]ethyl]diethylamine. Preparation, electrophilicity, and effects in MCF 7 breast cancer cells.,  32  (1): [PMID:2909731] [10.1021/jm00121a035]

Source

Source(1):

• Scientific Literature