4'-Methoxy-[2,3']bipyridinyl-4-carboxylic Acid [1-(2-Hydroxy-2-methyl-propyl)-1H-benzoimidazol-2-yl]-amide

ID: ALA4532034

PubChem CID: 139447554

Max Phase: Preclinical

Molecular Formula: C23H23N5O3

Molecular Weight: 417.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccncc1-c1cc(C(=O)/N=c2\[nH]c3ccccc3n2CC(C)(C)O)ccn1

Standard InChI:  InChI=1S/C23H23N5O3/c1-23(2,30)14-28-19-7-5-4-6-17(19)26-22(28)27-21(29)15-8-11-25-18(12-15)16-13-24-10-9-20(16)31-3/h4-13,30H,14H2,1-3H3,(H,26,27,29)

Standard InChI Key:  QWYLFZROSUGBFJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   19.3093  -15.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0173  -14.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7215  -15.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7215  -15.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0199  -16.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3093  -15.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5001  -16.2133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9857  -15.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5001  -14.8894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8010  -15.5515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2128  -14.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0323  -14.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4403  -14.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2562  -14.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6640  -14.8408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2612  -15.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4424  -15.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6689  -16.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4884  -16.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8934  -16.9630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4855  -17.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6719  -17.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2587  -16.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4392  -16.9695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0316  -17.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8010  -14.1312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7122  -17.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5041  -17.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7162  -18.0052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2982  -17.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7162  -16.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
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  3  9  1  0
  8 10  2  0
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 13 12  2  0
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 12 17  1  0
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 19 18  2  0
 20 19  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 11 26  2  0
  7 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4532034

   ---

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: 417.47

Molecular Weight (Monoisotopic): 417.1801

AlogP: 2.95

#Rotatable Bonds: 5

Polar Surface Area: 105.39

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.89

CX LogP: 2.02

CX LogD: 2.01

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.52

Np Likeness Score: -0.97

References

1. Engelhardt H, Böse D, Petronczki M, Scharn D, Bader G, Baum A, Bergner A, Chong E, Döbel S, Egger G, Engelhardt C, Ettmayer P, Fuchs JE, Gerstberger T, Gonnella N, Grimm A, Grondal E, Haddad N, Hopfgartner B, Kousek R, Krawiec M, Kriz M, Lamarre L, Leung J, Mayer M, Patel ND, Simov BP, Reeves JT, Schnitzer R, Schrenk A, Sharps B, Solca F, Stadtmüller H, Tan Z, Wunberg T, Zoephel A, McConnell DB..  (2019)  Start Selective and Rigidify: The Discovery Path toward a Next Generation of EGFR Tyrosine Kinase Inhibitors.,  62  (22): [PMID:31689114] [10.1021/acs.jmedchem.9b01169]

Source

Source(1):

• Scientific Literature