Ethyl (R)-2-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2'-oxo-[3,4'-bipyridin]-1'(2'H)-yl)acetate

ID: ALA4566804

PubChem CID: 155543509

Max Phase: Preclinical

Molecular Formula: C22H20Cl2FN3O4

Molecular Weight: 480.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)Cn1ccc(-c2cnc(N)c(O[C@H](C)c3c(Cl)ccc(F)c3Cl)c2)cc1=O

Standard InChI:  InChI=1S/C22H20Cl2FN3O4/c1-3-31-19(30)11-28-7-6-13(9-18(28)29)14-8-17(22(26)27-10-14)32-12(2)20-15(23)4-5-16(25)21(20)24/h4-10,12H,3,11H2,1-2H3,(H2,26,27)/t12-/m1/s1

Standard InChI Key:  YYIUNFDHPBMIHQ-GFCCVEGCSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   18.3652  -13.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3641  -13.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0789  -14.3444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7954  -13.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7925  -13.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0771  -12.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6514  -12.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6532  -11.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9428  -11.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2259  -11.8583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2242  -12.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9391  -13.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5104  -14.3424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9457  -10.6242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5054  -12.6853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5023  -11.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2152  -11.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9265  -11.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6389  -11.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6362  -10.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9151  -10.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2057  -10.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7863  -11.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9267  -12.6835    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.4873  -10.2197    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.3547  -11.8541    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.5129  -11.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7970  -11.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7940  -12.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0840  -11.4383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3680  -11.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6551  -11.4332    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  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4566804

   ---

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: 480.32

Molecular Weight (Monoisotopic): 479.0815

AlogP: 4.64

#Rotatable Bonds: 7

Polar Surface Area: 96.44

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.97

CX LogP: 3.62

CX LogD: 3.60

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -1.13

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