N2-(2-(4-Bromophenyl)-3-cyano-1,7-naphthyridin-4-yl)-2-methylalaninamid

ID: ALA5282610

Max Phase: Preclinical

Molecular Formula: C20H17BrN4O

Molecular Weight: 409.29

Names and Identifiers

Canonical SMILES:  CC(C)(CC(N)=O)c1c(C#N)c(-c2ccc(Br)cc2)nc2cnccc12

Standard InChI:  InChI=1S/C20H17BrN4O/c1-20(2,9-17(23)26)18-14-7-8-24-11-16(14)25-19(15(18)10-22)12-3-5-13(21)6-4-12/h3-8,11H,9H2,1-2H3,(H2,23,26)

Standard InChI Key:  ATWRIXADJZZHSM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   27.0846  -15.2077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8005  -14.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7976  -13.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0827  -13.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3702  -14.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3725  -13.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6603  -13.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9453  -13.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9469  -14.7968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6598  -15.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5078  -13.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2203  -13.1336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5116  -15.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5115  -16.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2253  -16.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9397  -16.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9357  -15.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2214  -14.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0792  -12.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3634  -12.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3599  -11.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6442  -11.0885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0722  -11.0824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6518  -16.4375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   27.4917  -12.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8997  -12.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  2  0
 11 12  3  0
  3 11  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  2 13  1  0
  4 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 16 24  1  0
 19 25  1  0
 19 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282610

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 409.29

Molecular Weight (Monoisotopic): 408.0586

AlogP: 4.08

#Rotatable Bonds: 4

Polar Surface Area: 92.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.25

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -0.82

References

1. Wortmann L, Bräuer N, Holton SJ, Irlbacher H, Weiske J, Lechner C, Meier R, Karén J, Siöberg CB, Pütter V, Christ CD, Ter Laak A, Lienau P, Lesche R, Nicke B, Cheung SH, Bauser M, Haegebarth A, von Nussbaum F, Mumberg D, Lemos C..  (2021)  Discovery and Characterization of the Potent and Highly Selective 1,7-Naphthyridine-Based Inhibitors BAY-091 and BAY-297 of the Kinase PIP4K2A.,  64  (21.0): [PMID:34699202] [10.1021/acs.jmedchem.1c01245]

Source

Source(1):

• Scientific Literature