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

ID: ALA4575832

PubChem CID: 129245476

Max Phase: Preclinical

Molecular Formula: C20H22N8O

Molecular Weight: 390.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1noc(-c2ccc3nc(Nc4cc(CN5CCNCC5)ccn4)[nH]c3c2)n1

Standard InChI:  InChI=1S/C20H22N8O/c1-13-23-19(29-27-13)15-2-3-16-17(11-15)25-20(24-16)26-18-10-14(4-5-22-18)12-28-8-6-21-7-9-28/h2-5,10-11,21H,6-9,12H2,1H3,(H2,22,24,25,26)

Standard InChI Key:  FQLDODIEEKFQOP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   21.5097  -17.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5086  -18.3189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2207  -18.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9345  -18.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9317  -17.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2189  -17.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7978  -17.0869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0860  -17.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3358  -17.1591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0013  -18.3081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1980  -18.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7898  -17.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9709  -17.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5591  -18.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9764  -19.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7939  -19.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6420  -17.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3512  -17.4864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3517  -18.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0610  -18.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7737  -18.3075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7726  -17.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0588  -17.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5693  -19.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7529  -19.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5868  -20.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3007  -21.2116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9093  -20.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8378  -21.1425    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
  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
M  END

Alternative Forms

1. Parent:

   

   ALA4575832

   ---

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: 390.45

Molecular Weight (Monoisotopic): 390.1917

AlogP: 2.47

#Rotatable Bonds: 5

Polar Surface Area: 107.79

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.14

CX Basic pKa: 9.21

CX LogP: 2.32

CX LogD: 0.60

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -1.64

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