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

ID: ALA3102939

PubChem CID: 72792827

Max Phase: Preclinical

Molecular Formula: C19H14N2O

Molecular Weight: 286.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccccc1-c1cnc2[nH]cc(-c3ccccc3)c2c1

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

Standard InChI Key:  CDOBVHIGUHJGGX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    2.4140  -13.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128  -14.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1272  -14.5575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1254  -12.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6998  -12.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8405  -13.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8408  -14.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307  -14.4014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1188  -13.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6303  -13.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181  -12.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8428  -12.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2310  -11.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7949  -10.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9666  -10.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5822  -11.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7030  -12.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9897  -11.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746  -12.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2775  -12.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9915  -13.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945  -14.1425    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
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3102939

   3-phenyl-5-(2-hydroxyphenyl)-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: 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: 9.64

CX Basic pKa: 2.84

CX LogP: 4.21

CX LogD: 4.21

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: -0.08

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