1-(4-(3-Nitrophenyl)piperazin-1-yl)-2-(3-(trifluoromethyl)phenoxy)ethanone

ID: ALA4474763

PubChem CID: 52458751

Max Phase: Preclinical

Molecular Formula: C19H18F3N3O4

Molecular Weight: 409.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(COc1cccc(C(F)(F)F)c1)N1CCN(c2cccc([N+](=O)[O-])c2)CC1

Standard InChI:  InChI=1S/C19H18F3N3O4/c20-19(21,22)14-3-1-6-17(11-14)29-13-18(26)24-9-7-23(8-10-24)15-4-2-5-16(12-15)25(27)28/h1-6,11-12H,7-10,13H2

Standard InChI Key:  LYQKSMJPDBWJMH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    1.6041   -1.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6029   -2.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -3.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0206   -2.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178   -1.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3092   -1.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7290   -3.1333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7260   -3.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4303   -4.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1398   -3.9518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -3.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4316   -2.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8466   -4.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448   -5.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5552   -3.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2620   -4.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9706   -3.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6764   -4.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3845   -3.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3868   -3.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6750   -2.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9698   -3.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -3.1335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8923   -3.9507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856   -2.7244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0912   -4.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0889   -5.1933    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.8000   -3.9694    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7968   -4.7835    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 23 24  2  0
 23 25  1  0
  2 23  1  0
 19 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4474763

   1-[4-(3-Nitrophenyl)piperazin-1-yl]-2-[3-(trifluoromethyl)phenoxy]ethanone

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 409.36

Molecular Weight (Monoisotopic): 409.1249

AlogP: 3.34

#Rotatable Bonds: 5

Polar Surface Area: 75.92

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.26

CX LogP: 3.49

CX LogD: 3.49

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: -2.00

References

1. Ragle LE, Palanisamy DJ, Joe MJ, Stein RS, Norman DD, Tigyi G, Baker DL, Parrill AL..  (2016)  Discovery and synthetic optimization of a novel scaffold for hydrophobic tunnel-targeted autotaxin inhibition.,  24  (19): [PMID:27544588] [10.1016/j.bmc.2016.08.004]

Source

Source(1):

• Scientific Literature