3,5-Di-(4-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine

ID: ALA3102943

PubChem CID: 72792685

Max Phase: Preclinical

Molecular Formula: C21H18N2O2

Molecular Weight: 330.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cnc3[nH]cc(-c4ccc(OC)cc4)c3c2)cc1

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

Standard InChI Key:  YZCFLKRLDGCOPV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    4.2816  -20.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2804  -21.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9952  -21.6971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9934  -20.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671  -20.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7087  -20.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7091  -21.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4994  -21.5408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9877  -20.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990  -20.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8869  -19.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7121  -19.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1003  -18.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6640  -18.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354  -18.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4509  -18.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5704  -19.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566  -18.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1413  -19.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441  -20.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8585  -20.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4263  -18.8078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250  -17.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0514  -17.2876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8758  -17.2589    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
M  END

Alternative Forms

1. Parent:

   

   ALA3102943

   3,5-bis(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: 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: 2.98

CX LogP: 4.20

CX LogD: 4.20

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -0.36

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