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

ID: ALA3102937

PubChem CID: 59699868

Max Phase: Preclinical

Molecular Formula: C19H14N2O

Molecular Weight: 286.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1cccc(-c2cnc3[nH]cc(-c4ccccc4)c3c2)c1

Standard InChI:  InChI=1S/C19H14N2O/c22-16-8-4-7-14(9-16)15-10-17-18(12-21-19(17)20-11-15)13-5-2-1-3-6-13/h1-12,22H,(H,20,21)

Standard InChI Key:  ITYVMPQOIASLBW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   33.0329   -8.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0317   -9.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7461  -10.2257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7443   -8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3188   -8.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4592   -8.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4595   -9.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2494  -10.0696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7376   -9.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2490   -8.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6368   -7.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4615   -7.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8495   -7.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4136   -6.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5853   -6.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2010   -7.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3220   -7.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6087   -7.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8937   -7.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8966   -8.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6105   -8.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1841   -8.9929    0.0000 O   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
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3102937

   3-(3-phenyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenol

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: 286.33

Molecular Weight (Monoisotopic): 286.1106

AlogP: 4.60

#Rotatable Bonds: 2

Polar Surface Area: 48.91

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.80

CX Basic pKa: 2.95

CX LogP: 4.21

CX LogD: 4.21

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: -0.12

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