(R)-6-Amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-1'-(2-(dimethylamino)ethyl)[3,4'-bipyridin]-2'(1'H)-one

ID: ALA4559485

PubChem CID: 155557858

Max Phase: Preclinical

Molecular Formula: C22H23Cl2FN4O2

Molecular Weight: 465.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H](Oc1cc(-c2ccn(CCN(C)C)c(=O)c2)cnc1N)c1c(Cl)ccc(F)c1Cl

Standard InChI:  InChI=1S/C22H23Cl2FN4O2/c1-13(20-16(23)4-5-17(25)21(20)24)31-18-10-15(12-27-22(18)26)14-6-7-29(19(30)11-14)9-8-28(2)3/h4-7,10-13H,8-9H2,1-3H3,(H2,26,27)/t13-/m1/s1

Standard InChI Key:  NFAGZVGAXFNBPX-CYBMUJFWSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   42.3605   -4.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3593   -5.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0674   -5.6570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.7770   -5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7742   -4.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0656   -4.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6534   -4.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6551   -3.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9514   -2.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2414   -3.1945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.2396   -4.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9479   -4.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4854   -5.6550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.9543   -1.9720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.4804   -4.0136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.4773   -3.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1834   -2.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8880   -3.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.5936   -2.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.5910   -1.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8768   -1.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1740   -1.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7680   -2.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8881   -4.0118    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   44.4624   -1.5714    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   47.3027   -3.1903    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   39.5351   -2.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8260   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1197   -2.7784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.1226   -1.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4106   -3.1845    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
  7  8  2  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
  1  7  1  0
  4 13  1  0
  9 14  2  0
  5 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
 16 23  1  6
 18 24  1  0
 22 25  1  0
 19 26  1  0
 10 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559485

   ---

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: 465.36

Molecular Weight (Monoisotopic): 464.1182

AlogP: 4.64

#Rotatable Bonds: 7

Polar Surface Area: 73.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.32

CX LogP: 3.66

CX LogD: 2.67

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.52

Np Likeness Score: -1.19

References

1. Chen W, Guo X, Zhang C, Ke D, Zhang G, Yu Y..  (2019)  Discovery of 2-aminopyridines bearing a pyridone moiety as potent ALK inhibitors to overcome the crizotinib-resistant mutants.,  183  [PMID:31569004] [10.1016/j.ejmech.2019.111734]

Source

Source(1):

• Scientific Literature