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

ID: ALA4536303

PubChem CID: 117872492

Max Phase: Preclinical

Molecular Formula: C22H25N7O3

Molecular Weight: 435.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1cc(NC(=O)c2cccc(-c3ccnc(NCC4CCOCC4)c3)n2)c(C(N)=O)n1

Standard InChI:  InChI=1S/C22H25N7O3/c1-29-13-18(20(28-29)21(23)30)27-22(31)17-4-2-3-16(26-17)15-5-8-24-19(11-15)25-12-14-6-9-32-10-7-14/h2-5,8,11,13-14H,6-7,9-10,12H2,1H3,(H2,23,30)(H,24,25)(H,27,31)

Standard InChI Key:  INTFQTHMHJDKBR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   38.4135  -14.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7041  -15.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7035  -16.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4117  -16.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1218  -16.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1189  -15.3099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.8309  -16.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8336  -17.3484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.5372  -16.1203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1272  -17.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3748  -17.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8300  -18.0412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.2409  -18.7476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.0396  -18.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6473  -19.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4778  -19.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4243  -18.8684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0170  -17.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4148  -14.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1242  -13.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1247  -12.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4166  -12.4558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7064  -12.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7094  -13.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8327  -12.4573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.5402  -12.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2482  -12.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9528  -12.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6587  -12.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6635  -11.6468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.9563  -11.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2442  -11.6417    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
 21 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536303

   US9586948, Example 17

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: 435.49

Molecular Weight (Monoisotopic): 435.2019

AlogP: 2.07

#Rotatable Bonds: 7

Polar Surface Area: 137.05

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.03

CX Basic pKa: 5.66

CX LogP: 1.85

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -1.54

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