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

ID: ALA142339

PubChem CID: 2968321

Max Phase: Preclinical

Molecular Formula: C21H25FN2O3

Molecular Weight: 372.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H25FN2O3/c1-16(25)20-4-2-3-5-21(20)27-15-19(26)14-23-10-12-24(13-11-23)18-8-6-17(22)7-9-18/h2-9,19,26H,10-15H2,1H3

Standard InChI Key:  DJQUTQXEFRSBMV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    9.7875   -5.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8667   -5.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5000   -5.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167   -7.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -5.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167   -5.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3792   -5.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9917   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -6.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542   -5.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2167   -5.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4875   -4.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6667   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2792   -6.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -5.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9167   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1917   -4.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9292   -5.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6292   -4.2917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -4.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -7.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167   -7.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -5.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3 15  1  0
  4  1  1  0
  5  2  1  0
  6  7  1  0
  7 17  1  0
  8  1  1  0
  9  1  1  0
 10  5  2  0
 11  3  1  0
 12  4  2  0
 13  4  1  0
 14  8  1  0
 15  9  1  0
 16 11  1  0
 17 16  1  0
 18 19  1  0
 19 13  2  0
 20 12  1  0
 21 18  1  0
 22 16  1  0
 23  2  2  0
 24  5  1  0
 25  6  2  0
 26 27  2  0
 27 25  1  0
  3 14  1  0
 20 18  2  0
 26 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA142339

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

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: 372.44

Molecular Weight (Monoisotopic): 372.1849

AlogP: 2.59

#Rotatable Bonds: 7

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: 6.63

CX LogP: 2.64

CX LogD: 2.57

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -1.46

References

1. Ecker G, Chiba P, Hitzler M, Schmid D, Visser K, Cordes HP, Csöllei J, Seydel JK, Schaper KJ..  (1996)  Structure-activity relationship studies on benzofuran analogs of propafenone-type modulators of tumor cell multidrug resistance.,  39  (24): [PMID:8941391] [10.1021/jm960384x]

2. 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]

3. 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]

4. Ecker GF and Chiba P. Structure-activity data for a series of P-glycoprotein inhibitors (Supplementary Data to CHEMBL1142990),  [10.6019/CHEMBL2449286]

Source

Source(2):

• Scientific Literature
• Deposited Supplementary Bioactivity Data