6-((5-Fluoropyridin-2-yl)amino)-4-((2-methoxy-3-(methylcarbamoyl)phenyl)-amino)-N-methylnicotinamide

ID: ALA4524832

PubChem CID: 155538766

Max Phase: Preclinical

Molecular Formula: C21H21FN6O3

Molecular Weight: 424.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cnc(Nc2ccc(F)cn2)cc1Nc1cccc(C(=O)NC)c1OC

Standard InChI:  InChI=1S/C21H21FN6O3/c1-23-20(29)13-5-4-6-15(19(13)31-3)27-16-9-18(26-11-14(16)21(30)24-2)28-17-8-7-12(22)10-25-17/h4-11H,1-3H3,(H,23,29)(H,24,30)(H2,25,26,27,28)

Standard InChI Key:  UBKKKDQKSNBDPK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   13.2098  -11.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2087  -12.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9167  -12.5206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6264  -12.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6236  -11.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9150  -10.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3348  -12.5186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0418  -12.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7468  -12.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4534  -12.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4526  -11.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7393  -10.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0356  -11.2938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1591  -10.8791    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.9125  -10.0660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5020  -10.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5018  -10.0664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7944  -11.2924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0866  -10.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6190   -9.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3258  -10.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0318   -9.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0298   -8.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3159   -8.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6128   -8.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9022   -8.4386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1975   -8.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3106   -7.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0156   -7.1994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6002   -7.2086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7260   -7.6034    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
 25 26  1  0
 26 27  1  0
 24 28  1  0
 28 29  1  0
 28 30  2  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4524832

   ---

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: 424.44

Molecular Weight (Monoisotopic): 424.1659

AlogP: 2.83

#Rotatable Bonds: 7

Polar Surface Area: 117.27

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.08

CX Basic pKa: 6.89

CX LogP: 3.04

CX LogD: 3.03

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.46

Np Likeness Score: -1.04

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]

2. Kato JY, Korenaga S, Iwakura M..  (2023)  Discovery of a potent and subtype-selective TYK2 degrader based on an allosteric TYK2 inhibitor.,  79  [PMID:36414177] [10.1016/j.bmcl.2022.129083]

Source

Source(1):

• Scientific Literature