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

ID: ALA3102941

PubChem CID: 59699998

Max Phase: Preclinical

Molecular Formula: C21H18N2O2

Molecular Weight: 330.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cnc3[nH]cc(-c4ccccc4)c3c2)cc1OC

Standard InChI:  InChI=1S/C21H18N2O2/c1-24-19-9-8-15(11-20(19)25-2)16-10-17-18(13-23-21(17)22-12-16)14-6-4-3-5-7-14/h3-13H,1-2H3,(H,22,23)

Standard InChI Key:  PTKRZXHHLCHSFE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   17.7937  -18.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7925  -18.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5074  -19.2769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5056  -17.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0792  -17.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2209  -18.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2212  -18.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0116  -19.1208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4999  -18.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0111  -17.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3991  -17.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2243  -17.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6125  -16.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1763  -15.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3476  -15.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9631  -16.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0824  -16.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3687  -16.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6534  -16.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6562  -17.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3705  -18.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9383  -16.3877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2245  -16.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9434  -18.0434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2273  -17.6336    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
 20 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3102941

   5-(3,4-dimethoxyphenyl)-3-phenyl-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: 330.39

Molecular Weight (Monoisotopic): 330.1368

AlogP: 4.91

#Rotatable Bonds: 4

Polar Surface Area: 47.14

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.96

CX LogP: 4.20

CX LogD: 4.20

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -0.33

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]

2. Verdonck S, Pu SY, Sorrell FJ, Elkins JM, Froeyen M, Gao LJ, Prugar LI, Dorosky DE, Brannan JM, Barouch-Bentov R, Knapp S, Dye JM, Herdewijn P, Einav S, De Jonghe S..  (2019)  Synthesis and Structure-Activity Relationships of 3,5-Disubstituted-pyrrolo[2,3- b]pyridines as Inhibitors of Adaptor-Associated Kinase 1 with Antiviral Activity.,  62  (12): [PMID:31136173] [10.1021/acs.jmedchem.9b00136]

Source

Source(1):

• Scientific Literature