3-(4-(tert-Butyl)benzamido)-5-chloropicolinic acid

ID: ALA4743039

PubChem CID: 162643753

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)cnc2C(=O)O)cc1

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

Standard InChI Key:  SOGATWAJQFUBEN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   14.0394   -2.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0383   -3.4114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7463   -3.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4560   -3.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4531   -2.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7445   -2.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7421   -1.3658    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.7461   -4.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0383   -5.0460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4537   -5.0463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1643   -3.8184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8714   -3.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5797   -3.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8701   -2.5915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5764   -4.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2839   -5.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9920   -4.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9880   -3.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2800   -3.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7008   -5.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7032   -5.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4074   -4.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4050   -5.4438    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
  4 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 13  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4743039

   ---

2. Alternative Forms:

   

   ALA4743039

   ---

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: 0.92

CX Basic pKa: 4.99

CX LogP: 3.46

CX LogD: 1.41

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.89

Np Likeness Score: -1.50

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