6-((5-Fluoropyridin-2-yl)amino)-4-((3-(methylcarbamoyl)-phenyl)-amino)-N-methyl-nicotinamide

ID: ALA4543090

PubChem CID: 121285026

Max Phase: Preclinical

Molecular Formula: C20H19FN6O2

Molecular Weight: 394.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cccc(Nc2cc(Nc3ccc(F)cn3)ncc2C(=O)NC)c1

Standard InChI:  InChI=1S/C20H19FN6O2/c1-22-19(28)12-4-3-5-14(8-12)26-16-9-18(25-11-15(16)20(29)23-2)27-17-7-6-13(21)10-24-17/h3-11H,1-2H3,(H,22,28)(H,23,29)(H2,24,25,26,27)

Standard InChI Key:  GSCIYRUDJIFMOT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   23.0739  -11.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0728  -12.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7808  -12.8260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4905  -12.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4876  -11.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7790  -11.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1988  -12.8240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9059  -12.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6109  -12.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3175  -12.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3167  -11.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6033  -11.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8997  -11.5992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0232  -11.1845    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.7766  -10.3714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3661  -11.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3659  -10.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6585  -11.5978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9507  -11.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4831   -9.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1899  -10.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8959   -9.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8939   -9.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1800   -8.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4769   -9.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1747   -7.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8797   -7.5048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4643   -7.5140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5901   -7.9088    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
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 11 14  1  0
  6 15  1  0
  1 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 15 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4543090

   ---

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: 394.41

Molecular Weight (Monoisotopic): 394.1554

AlogP: 2.82

#Rotatable Bonds: 6

Polar Surface Area: 108.04

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.12

CX Basic pKa: 5.96

CX LogP: 3.20

CX LogD: 3.18

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -1.41

References

1. Wrobleski ST, Moslin R, Lin S, Zhang Y, Spergel S, Kempson J, Tokarski JS, Strnad J, Zupa-Fernandez A, Cheng L, Shuster D, Gillooly K, Yang X, Heimrich E, McIntyre KW, Chaudhry C, Khan J, Ruzanov M, Tredup J, Mulligan D, Xie D, Sun H, Huang C, D'Arienzo C, Aranibar N, Chiney M, Chimalakonda A, Pitts WJ, Lombardo L, Carter PH, Burke JR, Weinstein DS..  (2019)  Highly Selective Inhibition of Tyrosine Kinase 2 (TYK2) for the Treatment of Autoimmune Diseases: Discovery of the Allosteric Inhibitor BMS-986165.,  62  (20): [PMID:31318208] [10.1021/acs.jmedchem.9b00444]

Source

Source(1):

• Scientific Literature