3-(4-(tert-Butyl)benzamido)-5-chloro-6-phenylpicolinic acid

ID: ALA4758848

PubChem CID: 162657738

Max Phase: Preclinical

Molecular Formula: C23H21ClN2O3

Molecular Weight: 408.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(C(=O)Nc2cc(Cl)c(-c3ccccc3)nc2C(=O)O)cc1

Standard InChI:  InChI=1S/C23H21ClN2O3/c1-23(2,3)16-11-9-15(10-12-16)21(27)25-18-13-17(24)19(26-20(18)22(28)29)14-7-5-4-6-8-14/h4-13H,1-3H3,(H,25,27)(H,28,29)

Standard InChI Key:  GTAAECNAGOJTLI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    4.8646   -9.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8634   -9.8540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715  -10.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2811   -9.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2783   -9.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5697   -8.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5673   -7.8084    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5713  -11.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8635  -11.4886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2789  -11.4889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1589   -8.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1600   -7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4530   -7.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444   -7.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -8.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4548   -9.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9895  -10.2610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6966   -9.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4049  -10.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6953   -9.0341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4016  -11.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1091  -11.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8171  -11.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8132  -10.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1051   -9.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5260  -11.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5284  -12.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2325  -11.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2302  -11.8864    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
  6  7  1  0
  3  8  1  0
  8  9  1  0
  8 10  2  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  1 11  1  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 19  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4758848

   ---

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: 408.89

Molecular Weight (Monoisotopic): 408.1241

AlogP: 5.65

#Rotatable Bonds: 4

Polar Surface Area: 79.29

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.89

CX Basic pKa: 4.84

CX LogP: 5.49

CX LogD: 3.39

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -1.14

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