6-Pyridin-4-yl-5-trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

ID: ALA2114202

PubChem CID: 10065195

Max Phase: Preclinical

Molecular Formula: C13H7F5N4O

Molecular Weight: 330.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1nc2cc(-c3ccncc3)c(C(F)(F)C(F)(F)F)[nH]c-2n1

Standard InChI:  InChI=1S/C13H7F5N4O/c14-12(15,13(16,17)18)9-7(6-1-3-19-4-2-6)5-8-10(21-9)22-11(23)20-8/h1-5H,(H2,20,21,22,23)

Standard InChI Key:  PESFXPODUIUSOI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    2.7750   -2.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -2.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1625   -2.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -0.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -1.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1583   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5875    0.3083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1583    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1625   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770   -3.4125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -3.4125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1625   -3.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9594   -1.9615    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1625   -1.3500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  1  0
  5  1  1  0
  6  4  1  0
  7  5  2  0
  8 10  1  0
  9  2  1  0
 10  9  2  0
 11  5  1  0
 12  8  1  0
 13 15  2  0
 14 16  2  0
 15 17  1  0
 16 12  1  0
 17 12  2  0
  9  7  1  0
  8  4  2  0
 13 14  1  0
  6 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
  6 22  1  0
  6 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2114202

   6-(4-Pyridinyl)-5-(1,1,2,2,2-pentafluoroethyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 330.22

Molecular Weight (Monoisotopic): 330.0540

AlogP: 3.33

#Rotatable Bonds: 2

Polar Surface Area: 74.69

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.29

CX Basic pKa: 4.55

CX LogP: 3.21

CX LogD: 3.20

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.71

Np Likeness Score: -0.64

References

1. Singh B, Bacon ER, Robinson S, Fritz RK, Lesher GY, Kumar V, Dority JA, Reuman M, Kuo GH, Eissenstat MA..  (1994)  Novel cAMP PDE III inhibitors: imidazo[4,5-b]pyridin-2(3H)-ones and thiazolo[4,5-b]pyridin-2(3H)-ones and their analogs.,  37  (2): [PMID:8295212] [10.1021/jm00028a007]

Source

Source(1):

• Scientific Literature