3-(3-(4-(Aminomethyl)phenyl)-6-bromo-3H-imidazo[4,5-b]-pyridin-2-yl)pyridin-2-amine Hydrochloride

ID: ALA4558319

PubChem CID: 60155269

Max Phase: Preclinical

Molecular Formula: C18H16BrClN6

Molecular Weight: 395.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.NCc1ccc(-n2c(-c3cccnc3N)nc3cc(Br)cnc32)cc1

Standard InChI:  InChI=1S/C18H15BrN6.ClH/c19-12-8-15-18(23-10-12)25(13-5-3-11(9-20)4-6-13)17(24-15)14-2-1-7-22-16(14)21;/h1-8,10H,9,20H2,(H2,21,22);1H

Standard InChI Key:  WOTDYAOFUWLYRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   25.0594  -14.1871    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.0130  -10.9227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4800  -10.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9736   -9.5859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2205  -10.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1981   -9.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4752   -9.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7742   -9.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8006  -10.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5240  -11.1219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3031  -10.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7356  -10.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5602  -10.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9534  -10.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5160   -9.4681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6927   -9.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2913  -11.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7549  -12.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0317  -13.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8449  -13.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3803  -12.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1005  -11.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2578   -8.7927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1233  -14.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9359  -14.1782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0470   -9.5177    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  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
  3 11  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  2 17  1  0
 16 23  1  0
 20 24  1  0
 24 25  1  0
  8 26  1  0
M  END

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: 395.26

Molecular Weight (Monoisotopic): 394.0542

AlogP: 3.29

#Rotatable Bonds: 3

Polar Surface Area: 95.64

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.34

CX LogP: 2.76

CX LogD: 0.83

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -1.18

References

1. Lapierre JM, Eathiraj S, Vensel D, Liu Y, Bull CO, Cornell-Kennon S, Iimura S, Kelleher EW, Kizer DE, Koerner S, Makhija S, Matsuda A, Moussa M, Namdev N, Savage RE, Szwaya J, Volckova E, Westlund N, Wu H, Schwartz B..  (2016)  Discovery of 3-(3-(4-(1-Aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine (ARQ 092): An Orally Bioavailable, Selective, and Potent Allosteric AKT Inhibitor.,  59  (13): [PMID:27305487] [10.1021/acs.jmedchem.6b00619]

Source

Source(1):

• Scientific Literature