N-(3-carbamoyl-1-methyl-1H-pyrazol-4-yl)-6'-morpholino-2,3'-bipyridine-6-carboxamide

ID: ALA4561018

PubChem CID: 117872334

Max Phase: Preclinical

Molecular Formula: C20H21N7O3

Molecular Weight: 407.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1cc(NC(=O)c2cccc(-c3ccc(N4CCOCC4)nc3)n2)c(C(N)=O)n1

Standard InChI:  InChI=1S/C20H21N7O3/c1-26-12-16(18(25-26)19(21)28)24-20(29)15-4-2-3-14(23-15)13-5-6-17(22-11-13)27-7-9-30-10-8-27/h2-6,11-12H,7-10H2,1H3,(H2,21,28)(H,24,29)

Standard InChI Key:  PJUYBXGWLSIRCS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   11.5824  -15.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8730  -15.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8724  -16.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5806  -16.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2907  -16.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2878  -15.6277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9998  -16.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0025  -17.6662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7061  -16.4381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2961  -18.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5437  -17.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9989  -18.3590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4098  -19.0654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2085  -18.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8161  -19.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6467  -20.2386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5932  -19.1862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1859  -18.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5836  -14.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2931  -13.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2936  -13.1832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5855  -12.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8753  -13.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8783  -14.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5846  -11.9564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2919  -11.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2929  -10.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5866  -10.3285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8775  -10.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8748  -11.5565    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
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 12 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
  1 19  1  0
 22 25  1  0
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4561018

   US9586948, Example 23

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: 407.43

Molecular Weight (Monoisotopic): 407.1706

AlogP: 1.06

#Rotatable Bonds: 5

Polar Surface Area: 128.26

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.03

CX Basic pKa: 5.49

CX LogP: 1.85

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -2.31

References

1. Hanisak J, Seganish WM, McElroy WT, Tang H, Zhang R, Tsui HC, Fischmann T, Tulshian D, Tata J, Sondey C, Devito K, Fossetta J, Garlisi CG, Lundell D, Niu X..  (2016)  Efforts towards the optimization of a bi-aryl class of potent IRAK4 inhibitors.,  26  (17): [PMID:27476420] [10.1016/j.bmcl.2016.07.048]

Source

Source(1):

• Scientific Literature