N-(3-(5-(3,4-dihydroxyphenyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)phenyl)acetamide

ID: ALA4875758

PubChem CID: 164629097

Max Phase: Preclinical

Molecular Formula: C20H16N4O3

Molecular Weight: 360.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cccc(-c2n[nH]c3ncc(-c4ccc(O)c(O)c4)cc23)c1

Standard InChI:  InChI=1S/C20H16N4O3/c1-11(25)22-15-4-2-3-13(7-15)19-16-8-14(10-21-20(16)24-23-19)12-5-6-17(26)18(27)9-12/h2-10,26-27H,1H3,(H,22,25)(H,21,23,24)

Standard InChI Key:  LEHDQJMFXABVJA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.5262  -28.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5250  -29.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2331  -29.8838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2313  -28.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399  -28.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401  -29.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7231  -29.7291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2068  -29.0629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7227  -28.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9748  -27.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7754  -27.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0278  -26.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4805  -26.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6776  -26.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4290  -27.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8204  -28.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8216  -27.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1146  -27.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4060  -27.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4088  -28.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1164  -28.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7027  -28.6619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6976  -27.0217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8271  -26.5060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3738  -27.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1732  -26.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1212  -27.8906    0.0000 O   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
  9 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
  1 16  1  0
 20 22  1  0
 19 23  1  0
 12 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875758

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 360.37

Molecular Weight (Monoisotopic): 360.1222

AlogP: 3.66

#Rotatable Bonds: 3

Polar Surface Area: 111.13

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.14

CX Basic pKa: 1.82

CX LogP: 2.76

CX LogD: 2.75

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.42

Np Likeness Score: -0.94

References

1. Park A, Hwang J, Lee JY, Heo EJ, Na YJ, Kang S, Jeong KS, Kim KY, Shin SJ, Lee H..  (2021)  Synthesis of novel 1H-Pyrazolo[3,4-b]pyridine derivatives as DYRK 1A/1B inhibitors.,  47  [PMID:34182093] [10.1016/j.bmcl.2021.128226]

Source

Source(1):

• Scientific Literature