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

ID: ALA3102946

PubChem CID: 72792757

Max Phase: Preclinical

Molecular Formula: C23H22N2O4

Molecular Weight: 390.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cnc3[nH]cc(-c4ccc(OC)c(OC)c4)c3c2)c(OC)c1

Standard InChI:  InChI=1S/C23H22N2O4/c1-26-16-6-7-17(21(11-16)28-3)15-9-18-19(13-25-23(18)24-12-15)14-5-8-20(27-2)22(10-14)29-4/h5-13H,1-4H3,(H,24,25)

Standard InChI Key:  RYIPFFFNGKQOMG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   32.6139  -23.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3286  -24.0484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3268  -22.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9004  -22.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0423  -22.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0425  -23.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8330  -23.8922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3213  -23.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   35.9977  -20.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1689  -20.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7844  -21.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   31.1917  -22.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7595  -21.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7582  -20.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3851  -19.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2095  -19.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1949  -23.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4819  -24.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2585  -21.0410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6944  -21.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  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
 13 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3102946

   5-(2,4-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)-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: 390.44

Molecular Weight (Monoisotopic): 390.1580

AlogP: 4.93

#Rotatable Bonds: 6

Polar Surface Area: 65.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.85

CX LogP: 3.89

CX LogD: 3.89

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -0.23

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. Lee S, Lee H, Kim J, Lee S, Kim SJ, Choi BS, Hong SS, Hong S..  (2014)  Development and biological evaluation of potent and selective c-KIT(D816V) inhibitors.,  57  (15): [PMID:25004409] [10.1021/jm500413g]

Source

Source(1):

• Scientific Literature