2-(4-(2-(2-(Trifluoromethyl)phenoxy)acetyl)piperazin-1-yl)benzoic acid

ID: ALA4520630

PubChem CID: 155542373

Max Phase: Preclinical

Molecular Formula: C20H19F3N2O4

Molecular Weight: 408.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccccc1N1CCN(C(=O)COc2ccccc2C(F)(F)F)CC1

Standard InChI:  InChI=1S/C20H19F3N2O4/c21-20(22,23)15-6-2-4-8-17(15)29-13-18(26)25-11-9-24(10-12-25)16-7-3-1-5-14(16)19(27)28/h1-8H,9-13H2,(H,27,28)

Standard InChI Key:  PASWGUCQEVJLCV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.8847  -18.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8836  -19.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5916  -20.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3013  -19.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2985  -18.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5898  -18.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0096  -20.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0067  -20.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7109  -21.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204  -20.9477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4211  -20.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7123  -19.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1272  -21.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1254  -22.1751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8358  -20.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5426  -21.3610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2512  -20.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9571  -21.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6652  -20.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6675  -20.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9557  -19.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2505  -20.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914  -20.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8836  -21.3568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2990  -21.3571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9533  -22.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2437  -22.5903    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.6591  -22.5969    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.9478  -23.0010    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
  3 23  1  0
 23 24  1  0
 23 25  2  0
 18 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4520630

   ---

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: 408.38

Molecular Weight (Monoisotopic): 408.1297

AlogP: 3.13

#Rotatable Bonds: 5

Polar Surface Area: 70.08

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.54

CX Basic pKa: 0.11

CX LogP: 3.21

CX LogD: 0.43

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.82

Np Likeness Score: -1.39

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