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

ID: ALA3102956

PubChem CID: 72792898

Max Phase: Preclinical

Molecular Formula: C19H14N2O2

Molecular Weight: 302.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1cccc(-c2cnc3[nH]cc(-c4cccc(O)c4)c3c2)c1

Standard InChI:  InChI=1S/C19H14N2O2/c22-15-5-1-3-12(7-15)14-9-17-18(11-21-19(17)20-10-14)13-4-2-6-16(23)8-13/h1-11,22-23H,(H,20,21)

Standard InChI Key:  MACHJSMEPKMVPA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   25.1134  -13.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1123  -14.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8269  -14.7117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8252  -13.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3990  -13.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5404  -13.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5406  -14.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3309  -14.5556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8191  -13.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3305  -13.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7184  -12.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5434  -12.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9316  -11.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4953  -11.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6669  -11.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2824  -11.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4024  -12.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6888  -11.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9736  -12.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9764  -13.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6906  -13.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2637  -13.4784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7559  -11.7050    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
 13 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3102956

   3-[3-(3-hydroxyphenyl)-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: 302.33

Molecular Weight (Monoisotopic): 302.1055

AlogP: 4.31

#Rotatable Bonds: 2

Polar Surface Area: 69.14

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.48

CX Basic pKa: 2.95

CX LogP: 3.91

CX LogD: 3.91

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.52

Np Likeness Score: -0.05

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