3-(4-(2-(3,5-Dichlorophenoxy)acetyl)piperazin-1-yl)benzoic acid

ID: ALA4519920

PubChem CID: 155542201

Max Phase: Preclinical

Molecular Formula: C19H18Cl2N2O4

Molecular Weight: 409.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc(N2CCN(C(=O)COc3cc(Cl)cc(Cl)c3)CC2)c1

Standard InChI:  InChI=1S/C19H18Cl2N2O4/c20-14-9-15(21)11-17(10-14)27-12-18(24)23-6-4-22(5-7-23)16-3-1-2-13(8-16)19(25)26/h1-3,8-11H,4-7,12H2,(H,25,26)

Standard InChI Key:  WOZCYXSWTTYEKQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   12.3431  -12.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3420  -13.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0500  -14.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7597  -13.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7569  -12.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0482  -12.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4680  -14.0539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4651  -14.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1693  -15.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8788  -14.8725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8795  -14.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1707  -13.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5856  -15.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5838  -16.0998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2942  -14.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0010  -15.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7096  -14.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4155  -15.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1236  -14.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1258  -14.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4141  -13.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7089  -14.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6339  -14.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9266  -13.6458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6333  -14.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8302  -15.2967    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.4130  -12.8409    0.0000 Cl  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
  2 23  1  0
 23 24  2  0
 23 25  1  0
 19 26  1  0
 21 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4519920

   ---

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: 409.27

Molecular Weight (Monoisotopic): 408.0644

AlogP: 3.42

#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: 4.76

CX Basic pKa: 2.40

CX LogP: 3.54

CX LogD: 0.95

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -1.47

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