(3-(3,4-dichlorophenyl)-3H-imidazo[4,5-b]pyridin-2-yl)(2,7-diazaspiro[3.5]nonan-2-yl)methanone

ID: ALA4745399

PubChem CID: 162647840

Max Phase: Preclinical

Molecular Formula: C20H19Cl2N5O

Molecular Weight: 416.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(c1nc2cccnc2n1-c1ccc(Cl)c(Cl)c1)N1CC2(CCNCC2)C1

Standard InChI:  InChI=1S/C20H19Cl2N5O/c21-14-4-3-13(10-15(14)22)27-17-16(2-1-7-24-17)25-18(27)19(28)26-11-20(12-26)5-8-23-9-6-20/h1-4,7,10,23H,5-6,8-9,11-12H2

Standard InChI Key:  GVURIKUOZVVGMD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   23.5789  -21.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1661  -22.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5687  -22.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3857  -22.9094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7984  -22.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3942  -21.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0911  -19.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0900  -20.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7980  -20.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7963  -18.9891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5049  -19.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5097  -20.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2897  -20.4614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7671  -19.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2819  -19.1369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5842  -19.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9970  -20.4967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9887  -19.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5304  -18.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3300  -18.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5781  -17.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0275  -16.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2256  -16.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9813  -17.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2744  -16.0265    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.3765  -17.2363    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.7903  -21.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7877  -20.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 15 19  1  0
 22 25  1  0
 21 26  1  0
 17 27  1  0
 27  1  1  0
  1 28  1  0
 28 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4745399

   ---

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: 416.31

Molecular Weight (Monoisotopic): 415.0967

AlogP: 3.55

#Rotatable Bonds: 2

Polar Surface Area: 63.05

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.02

CX LogP: 2.89

CX LogD: 0.37

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: -1.38

References

1. Vadukoot AK,Sharma S,Aretz CD,Kumar S,Gautam N,Alnouti Y,Aldrich AL,Heim CE,Kielian T,Hopkins CR.  (2020)  Synthesis and SAR Studies of 1H-Pyrrolo[2,3-b]pyridine-2-carboxamides as Phosphodiesterase 4B (PDE4B) Inhibitors.,  11  (10): [PMID:33062163] [10.1021/acsmedchemlett.9b00369]

Source

Source(1):

• Scientific Literature