3-{4-[6-Amino-5-(4-chlorophenyl)pyridin-3-yl]phenoxy}-2,2-dimethylpropanoic acid

ID: ALA4780287

PubChem CID: 162662678

Max Phase: Preclinical

Molecular Formula: C22H21ClN2O3

Molecular Weight: 396.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(COc1ccc(-c2cnc(N)c(-c3ccc(Cl)cc3)c2)cc1)C(=O)O

Standard InChI:  InChI=1S/C22H21ClN2O3/c1-22(2,21(26)27)13-28-18-9-5-14(6-10-18)16-11-19(20(24)25-12-16)15-3-7-17(23)8-4-15/h3-12H,13H2,1-2H3,(H2,24,25)(H,26,27)

Standard InChI Key:  GRSMVVJJBSUIMU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   16.5172   -5.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1127   -4.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7037   -5.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8185   -4.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5288   -4.7991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3623   -2.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3612   -3.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0692   -3.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7789   -3.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7761   -2.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0674   -1.9395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4837   -3.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4837   -4.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1912   -4.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8992   -4.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8953   -3.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1872   -3.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4822   -1.9335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6550   -3.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9474   -3.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2398   -3.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2387   -4.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9511   -4.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6557   -4.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6081   -4.7966    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.4063   -4.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4044   -3.5682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6947   -4.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  9 12  1  0
 10 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  7 19  1  0
 15 25  1  0
 22  5  1  0
  5  4  1  0
  4  2  1  0
  2 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4780287

   ---

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: 396.87

Molecular Weight (Monoisotopic): 396.1241

AlogP: 5.14

#Rotatable Bonds: 6

Polar Surface Area: 85.44

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.19

CX Basic pKa: 6.03

CX LogP: 3.57

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: -0.46

References

1. Dow RL,Ammirati M,Bagley SW,Bhattacharya SK,Buckbinder L,Cortes C,El-Kattan AF,Ford K,Freeman GB,Guimarães CRW,Liu S,Niosi M,Skoura A,Tess D.  (2018)  2-Aminopyridine-Based Mitogen-Activated Protein Kinase Kinase Kinase Kinase 4 (MAP4K4) Inhibitors: Assessment of Mechanism-Based Safety.,  61  (7): [PMID:29570292] [10.1021/acs.jmedchem.8b00152]

Source

Source(1):

• Scientific Literature