N-(3-carbamoyl-1-methyl-1H-pyrazol-4-yl)-5'-chloro-2,3'-bipyridine-6-carboxamide

ID: ALA4559589

PubChem CID: 117873092

Max Phase: Preclinical

Molecular Formula: C16H13ClN6O2

Molecular Weight: 356.77

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1cc(NC(=O)c2cccc(-c3cncc(Cl)c3)n2)c(C(N)=O)n1

Standard InChI:  InChI=1S/C16H13ClN6O2/c1-23-8-13(14(22-23)15(18)24)21-16(25)12-4-2-3-11(20-12)9-5-10(17)7-19-6-9/h2-8H,1H3,(H2,18,24)(H,21,25)

Standard InChI Key:  HVOIKNMEWFMNPX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    1.9536  -19.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2441  -19.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2436  -20.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9517  -21.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6619  -20.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6590  -19.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3709  -21.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736  -21.8677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0773  -20.6396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673  -22.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148  -21.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700  -22.5605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7810  -23.2669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797  -23.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873  -23.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0179  -24.4401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9644  -23.3877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5570  -22.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548  -18.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643  -18.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6648  -17.3847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567  -16.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2465  -17.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2494  -18.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375  -16.9816    0.0000 Cl  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
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559589

   US9586948, Example 29

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: 356.77

Molecular Weight (Monoisotopic): 356.0789

AlogP: 1.88

#Rotatable Bonds: 4

Polar Surface Area: 115.79

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.03

CX Basic pKa: 2.47

CX LogP: 1.97

CX LogD: 1.97

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -2.12

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