4-(4-(tert-Butyl)benzamido)-6-chloronicotinic acid

ID: ALA4754068

PubChem CID: 162654125

Max Phase: Preclinical

Molecular Formula: C17H17ClN2O3

Molecular Weight: 332.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(C(=O)Nc2cc(Cl)ncc2C(=O)O)cc1

Standard InChI:  InChI=1S/C17H17ClN2O3/c1-17(2,3)11-6-4-10(5-7-11)15(21)20-13-8-14(18)19-9-12(13)16(22)23/h4-9H,1-3H3,(H,22,23)(H,19,20,21)

Standard InChI Key:  AYIBPZCBXBEWFO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   34.0235  -20.9002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0223  -21.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7304  -22.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4400  -21.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4372  -20.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7286  -20.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7302  -22.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0223  -23.3544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4378  -23.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1484  -22.1268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8554  -21.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5638  -22.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8541  -20.8999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5604  -22.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2680  -23.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9760  -22.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9721  -22.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2640  -21.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6849  -23.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7261  -19.6742    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.6873  -24.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3914  -22.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3891  -23.7522    0.0000 C   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
  3  7  1  0
  7  8  1  0
  7  9  2  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 12  1  0
 16 19  1  0
  6 20  1  0
 19 21  1  0
 19 22  1  0
 19 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4754068

   ---

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: 332.79

Molecular Weight (Monoisotopic): 332.0928

AlogP: 3.98

#Rotatable Bonds: 3

Polar Surface Area: 79.29

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.94

CX Basic pKa: 1.19

CX LogP: 4.52

CX LogD: 1.33

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.83

Np Likeness Score: -1.37

References

1. Khalifa MM,Martorelli Di Genova B,McAlpine SG,Gallego-Lopez GM,Stevenson DM,Rozema SD,Monaghan NP,Morris JC,Knoll LJ,Golden JE.  (2020)  Dual-Stage Picolinic Acid-Derived Inhibitors of Toxoplasma gondii.,  11  (12): [PMID:33335660] [10.1021/acsmedchemlett.0c00267]

Source

Source(1):

• Scientific Literature