4-(3-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzene-1,2-diol

ID: ALA4292553

Cas Number: 1614314-22-5

PubChem CID: 90248517

Max Phase: Preclinical

Molecular Formula: C19H13FN2O2

Molecular Weight: 320.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(-c2cnc3[nH]cc(-c4ccc(F)cc4)c3c2)cc1O

Standard InChI:  InChI=1S/C19H13FN2O2/c20-14-4-1-11(2-5-14)16-10-22-19-15(16)7-13(9-21-19)12-3-6-17(23)18(24)8-12/h1-10,23-24H,(H,21,22)

Standard InChI Key:  IRJDHVRCNAUAOH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   12.1615  -17.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1604  -18.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8684  -19.1283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8666  -17.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5753  -17.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5801  -18.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3645  -18.9691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8445  -18.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3566  -17.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4558  -17.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4569  -16.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7500  -16.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0414  -16.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0442  -17.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7517  -17.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6025  -16.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4022  -16.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6502  -15.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0996  -15.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2977  -15.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0534  -16.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7502  -15.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3330  -16.2662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3465  -14.5277    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  1 10  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  9 16  1  0
 12 22  1  0
 13 23  1  0
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4292553

   Fluoro-DANDY

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: 320.32

Molecular Weight (Monoisotopic): 320.0961

AlogP: 4.45

#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: 9.16

CX Basic pKa: 2.97

CX LogP: 4.05

CX LogD: 4.04

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.48

Np Likeness Score: -0.26

References

1. Jarhad DB, Mashelkar KK, Kim HR, Noh M, Jeong LS..  (2018)  Dual-Specificity Tyrosine Phosphorylation-Regulated Kinase 1A (DYRK1A) Inhibitors as Potential Therapeutics.,  61  (22): [PMID:29985601] [10.1021/acs.jmedchem.8b00185]

2. Liu T, Wang Y, Wang J, Ren C, Chen H, Zhang J..  (2022)  DYRK1A inhibitors for disease therapy: Current status and perspectives.,  229  [PMID:34954592] [10.1016/j.ejmech.2021.114062]

3. Lindberg MF, Deau E, Arfwedson J, George N, George P, Alfonso P, Corrionero A, Meijer L..  (2023)  Comparative Efficacy and Selectivity of Pharmacological Inhibitors of DYRK and CLK Protein Kinases.,  66  (6): [PMID:36876904] [10.1021/acs.jmedchem.2c02068]

Source

Source(1):

• Scientific Literature