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

ID: ALA5196629

PubChem CID: 90248518

Max Phase: Preclinical

Molecular Formula: C19H12F2N2O2

Molecular Weight: 338.31

Names and Identifiers

Canonical SMILES:  Oc1ccc(-c2cnc3[nH]cc(-c4ccc(F)c(F)c4)c3c2)cc1O

Standard InChI:  InChI=1S/C19H12F2N2O2/c20-15-3-1-11(6-16(15)21)14-9-23-19-13(14)5-12(8-22-19)10-2-4-17(24)18(25)7-10/h1-9,24-25H,(H,22,23)

Standard InChI Key:  SZRVXIVKDKMTQJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -0.2889   -1.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4256   -0.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1374   -1.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1374   -1.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274   -2.3389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2889   -1.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9221   -2.1821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9222   -0.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4072   -1.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1358   -0.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036   -0.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7184   -1.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4305   -0.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4305    0.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202    0.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036    0.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5524    0.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661    1.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5634    1.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451    0.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363    0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.3389    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202    1.3723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1451    0.5479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826    1.9117    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  4  7  1  0
  3  8  1  0
  8  9  2  0
  9  7  1  0
  8 10  1  0
  1 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 11 16  1  0
 17 10  2  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 10 21  1  0
 19 22  1  0
 15 23  1  0
 14 24  1  0
 18 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5196629

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

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 338.31

Molecular Weight (Monoisotopic): 338.0867

AlogP: 4.59

#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: 2.96

CX LogP: 4.19

CX LogD: 4.19

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.47

Np Likeness Score: -0.50

References

1. 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]

Source

Source(1):

• Scientific Literature