N-(4-{[4-(2,2-Difluoroethyl)piperazin-1-yl]methyl}pyridin-2-yl)-6-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-benzimidazol-2-amine

ID: ALA4587843

PubChem CID: 155567366

Max Phase: Preclinical

Molecular Formula: C22H24F2N8O

Molecular Weight: 454.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1noc(-c2ccc3nc(Nc4cc(CN5CCN(CC(F)F)CC5)ccn4)[nH]c3c2)n1

Standard InChI:  InChI=1S/C22H24F2N8O/c1-14-26-21(33-30-14)16-2-3-17-18(11-16)28-22(27-17)29-20-10-15(4-5-25-20)12-31-6-8-32(9-7-31)13-19(23)24/h2-5,10-11,19H,6-9,12-13H2,1H3,(H2,25,27,28,29)

Standard InChI Key:  WNLZXWKRUIEXHK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   34.4774  -25.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4763  -26.3175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1885  -26.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9023  -26.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8994  -25.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1867  -25.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7655  -25.0854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0579  -25.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3077  -25.1576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9691  -26.3066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1657  -26.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7576  -25.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9387  -25.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5269  -26.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9441  -27.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7617  -27.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6097  -25.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3231  -25.4849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3236  -26.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0329  -26.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7456  -26.3060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7445  -25.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0307  -25.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5411  -27.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7247  -27.9966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5546  -28.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2684  -29.2102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8771  -28.6563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8055  -29.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4533  -26.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4533  -27.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7456  -27.9487    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   40.1651  -27.9487    0.0000 F   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
  1  7  1  0
  7  8  1  0
  8  9  2  0
  9 12  1  0
 11 10  1  0
 10  8  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 24  1  0
 15 24  1  0
 26 29  1  0
 21 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4587843

   ---

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: 454.49

Molecular Weight (Monoisotopic): 454.2041

AlogP: 3.44

#Rotatable Bonds: 7

Polar Surface Area: 99.00

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.14

CX Basic pKa: 6.26

CX LogP: 3.13

CX LogD: 3.09

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.44

Np Likeness Score: -1.83

References

1. Lefranc J, Schulze VK, Hillig RC, Briem H, Prinz F, Mengel A, Heinrich T, Balint J, Rengachari S, Irlbacher H, Stöckigt D, Bömer U, Bader B, Gradl SN, Nising CF, von Nussbaum F, Mumberg D, Panne D, Wengner AM..  (2020)  Discovery of BAY-985, a Highly Selective TBK1/IKKε Inhibitor.,  63  (2): [PMID:31859507] [10.1021/acs.jmedchem.9b01460]

Source

Source(1):

• Scientific Literature