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

ID: ALA146565

Cas Number: 214627-82-4

PubChem CID: 4447723

Max Phase: Preclinical

Molecular Formula: C21H25FN2O3

Molecular Weight: 372.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccc(OCC(O)CN2CCN(c3ccc(F)cc3)CC2)cc1

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

Standard InChI Key:  HCPYODFBLHRECO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   12.7206   -2.3069    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5759    0.1681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0049   -0.6569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0036    1.4056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8628   -0.6569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4338    0.1681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5772   -1.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1483   -1.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8628    0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4338   -0.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1483    0.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2917   -0.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5772   -1.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7193    0.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615    0.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0049    0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325    1.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0062   -1.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0062   -1.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2917   -2.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470    0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615    1.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2904    0.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325    0.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470    1.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180    1.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180    2.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0
  2 15  1  0
  2 23  1  0
  3 16  1  0
  4 26  2  0
  5  7  1  0
  5  8  1  0
  5  9  1  0
  6 10  1  0
  6 11  1  0
  6 14  1  0
  7 12  2  0
  7 13  1  0
  8 10  1  0
  9 11  1  0
 12 19  1  0
 13 20  2  0
 14 16  1  0
 15 21  2  0
 15 22  1  0
 16 23  1  0
 17 24  2  0
 17 25  1  0
 17 26  1  0
 18 19  2  0
 18 20  1  0
 21 24  1  0
 22 25  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA146565

   1-(4-{3-[4-(4-Fluorophenyl)piperazin-1-yl]-2-hydroxypropoxy}phenyl)ethanone

2. Alternative Forms:

   

   ALA146565

   1-[4-[3-[4-(4-Fluorophenyl)piperazin-1-yl]-2-hydroxypropoxy]phenyl]ethanone;hydrochloride

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: 6.67

CX LogP: 2.64

CX LogD: 2.57

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -1.47

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]

Source

Source(1):

• Scientific Literature