(2-{3-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-2-hydroxy-propoxy}-phenyl)-phenyl-methanone

ID: ALA148318

PubChem CID: 10598951

Max Phase: Preclinical

Molecular Formula: C26H27FN2O3

Molecular Weight: 434.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccccc1)c1ccccc1OCC(O)CN1CCN(c2ccc(F)cc2)CC1

Standard InChI:  InChI=1S/C26H27FN2O3/c27-21-10-12-22(13-11-21)29-16-14-28(15-17-29)18-23(30)19-32-25-9-5-4-8-24(25)26(31)20-6-2-1-3-7-20/h1-13,23,30H,14-19H2

Standard InChI Key:  UHWBVAVSBQYTQW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    3.2042   -1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2000    0.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750   -0.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9125    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -1.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -0.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2000   -0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0625   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6292    0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9125    1.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6292   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3417    1.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6250    1.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3417    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0542    1.9875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4875   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417    0.3333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4875   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750   -1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -4.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -4.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750   -0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250   -4.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 10  1  0
  4 12  1  0
  5  3  1  0
  6  1  1  0
  7  2  2  0
  8  6  1  0
  9 15  1  0
 10 16  1  0
 11  2  1  0
 12 17  1  0
 13  5  2  0
 14  5  1  0
 15  4  1  0
 16  4  1  0
 17 18  1  0
 18  8  1  0
 19 20  1  0
 20 14  2  0
 21 13  1  0
 22 19  1  0
 23  1  2  0
 24 17  1  0
 25  6  2  0
 26 11  2  0
 27 11  1  0
 28 23  1  0
 29 26  1  0
 30 27  2  0
 31 28  2  0
 32 30  1  0
 31 25  1  0
 32 29  2  0
  3  9  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA148318

   (2-(3-(4-(4-Fluorophenyl)piperazin-1-yl)-2-hydroxypropoxy)phenyl)(phenyl)methanone

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: 434.51

Molecular Weight (Monoisotopic): 434.2006

AlogP: 3.62

#Rotatable Bonds: 8

Polar Surface Area: 53.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.62

CX LogP: 4.54

CX LogD: 4.48

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.55

Np Likeness Score: -1.34

References

1. Fleischer R, Wiese M..  (2003)  Three-dimensional quantitative structure-activity relationship analysis of propafenone-type multidrug resistance modulators: influence of variable selection on test set predictivity.,  46  (23): [PMID:14584949] [10.1021/jm030876r]

2. Kaiser D, Terfloth L, Kopp S, Schulz J, de Laet R, Chiba P, Ecker GF, Gasteiger J..  (2007)  Self-organizing maps for identification of new inhibitors of P-glycoprotein.,  50  (7): [PMID:17352460] [10.1021/jm060604z]

3. Jabeen I, Pleban K, Rinner U, Chiba P, Ecker GF..  (2012)  Structure-activity relationships, ligand efficiency, and lipophilic efficiency profiles of benzophenone-type inhibitors of the multidrug transporter P-glycoprotein.,  55  (7): [PMID:22452412] [10.1021/jm201705f]

Source

Source(1):

• Scientific Literature