3-(4-Methoxyphenyl)-5-(2,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridine

ID: ALA3102944

PubChem CID: 72792756

Max Phase: Preclinical

Molecular Formula: C22H20N2O3

Molecular Weight: 360.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2c[nH]c3ncc(-c4ccc(OC)cc4OC)cc23)cc1

Standard InChI:  InChI=1S/C22H20N2O3/c1-25-16-6-4-14(5-7-16)20-13-24-22-19(20)10-15(12-23-22)18-9-8-17(26-2)11-21(18)27-3/h4-13H,1-3H3,(H,23,24)

Standard InChI Key:  KFDRCCYTVOCUEC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   14.0400  -21.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0389  -22.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7536  -22.4773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7519  -20.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3254  -20.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4673  -21.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4675  -22.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2579  -22.3211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7463  -21.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2575  -20.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6455  -20.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4707  -20.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8590  -19.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4227  -18.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5939  -18.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2095  -19.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3288  -19.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6150  -19.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8997  -19.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9025  -20.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6168  -21.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1845  -19.5880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1833  -18.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8100  -18.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6345  -18.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6199  -22.0621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9069  -22.4772    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
 19 22  1  0
 22 23  1  0
 14 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3102944

   5-(2,4-dimethoxyphenyl)-3-(4-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: 360.41

Molecular Weight (Monoisotopic): 360.1474

AlogP: 4.92

#Rotatable Bonds: 5

Polar Surface Area: 56.37

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.85

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.55

Np Likeness Score: -0.28

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