3-Phenyl-5-(2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine

ID: ALA3102938

PubChem CID: 72792688

Max Phase: Preclinical

Molecular Formula: C20H16N2O

Molecular Weight: 300.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1-c1cnc2[nH]cc(-c3ccccc3)c2c1

Standard InChI:  InChI=1S/C20H16N2O/c1-23-19-10-6-5-9-16(19)15-11-17-18(13-22-20(17)21-12-15)14-7-3-2-4-8-14/h2-13H,1H3,(H,21,22)

Standard InChI Key:  WLSORYWMNHIFJW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   39.8409   -9.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8397  -10.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5542  -10.7401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.5524   -9.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1265   -9.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2675   -9.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2677  -10.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0579  -10.5838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.5460   -9.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0575   -9.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4453   -8.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2702   -8.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6583   -7.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2221   -7.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3938   -7.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0094   -7.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1298   -8.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4164   -7.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7013   -8.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7041   -9.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4182   -9.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4212  -10.3249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.7085  -10.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  7  2  0
  6  4  2  0
  4  1  1  0
  1  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
 10 11  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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  5  1  0
 21 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3102938

   3-phenyl-5-(2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine

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: 300.36

Molecular Weight (Monoisotopic): 300.1263

AlogP: 4.91

#Rotatable Bonds: 3

Polar Surface Area: 37.91

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.83

CX LogP: 4.36

CX LogD: 4.36

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: -0.40

References

1. Gourdain S, Dairou J, Denhez C, Bui LC, Rodrigues-Lima F, Janel N, Delabar JM, Cariou K, Dodd RH..  (2013)  Development of DANDYs, new 3,5-diaryl-7-azaindoles demonstrating potent DYRK1A kinase inhibitory activity.,  56  (23): [PMID:24188002] [10.1021/jm401049v]

Source

Source(1):

• Scientific Literature