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

ID: ALA3102940

PubChem CID: 72792755

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)c(OC)c1

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

Standard InChI Key:  BBRDOLSLQNRECU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.3359  -13.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3347  -14.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0496  -15.1566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0478  -13.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6214  -13.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7631  -13.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7634  -14.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5538  -15.0005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0421  -14.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5534  -13.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9414  -12.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7666  -12.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1548  -12.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7185  -11.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8899  -11.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5053  -12.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6246  -12.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9109  -12.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1955  -12.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1983  -13.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9127  -13.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9157  -14.7414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2028  -15.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4804  -12.2672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4791  -11.4422    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
 19 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3102940

   5-(2,4-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: 2.85

CX LogP: 4.20

CX LogD: 4.20

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -0.35

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