6-(2,5-dimethylfuran-3-yl)-2-phenyl-1H-pyrazolo[3,4-b]pyridin-3(2H)-one

ID: ALA4238380

PubChem CID: 39047495

Max Phase: Preclinical

Molecular Formula: C18H15N3O2

Molecular Weight: 305.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2ccc3c(=O)n(-c4ccccc4)[nH]c3n2)c(C)o1

Standard InChI:  InChI=1S/C18H15N3O2/c1-11-10-15(12(2)23-11)16-9-8-14-17(19-16)20-21(18(14)22)13-6-4-3-5-7-13/h3-10H,1-2H3,(H,19,20)

Standard InChI Key:  BHJCGOXOUGUHEX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    5.1948  -19.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1936  -20.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9017  -20.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8999  -19.1129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6085  -19.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6133  -20.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3977  -20.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8777  -19.9223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3899  -19.2593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6547  -21.3668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6949  -19.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4870  -19.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4008  -18.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014  -18.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1930  -18.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7400  -19.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1050  -20.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9214  -20.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3267  -19.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9095  -19.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0944  -19.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0079  -17.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3803  -18.9207    0.0000 C   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  1  0
  9  5  1  0
  7 10  2  0
  8 11  1  0
  1 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 12  1  0
 11 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 11  1  0
 13 22  1  0
 15 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4238380

   6-(2,5-dimethylfuran-3-yl)-2-phenyl-1H-pyrazolo[3,4-b]pyridin-3(2H)-one

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: 305.34

Molecular Weight (Monoisotopic): 305.1164

AlogP: 3.59

#Rotatable Bonds: 2

Polar Surface Area: 63.82

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.28

CX Basic pKa: 2.26

CX LogP: 4.43

CX LogD: 4.38

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.62

Np Likeness Score: -1.03

References

1. Hajdú I, Kardos J, Major B, Fabó G, Lőrincz Z, Cseh S, Dormán G..  (2018)  Inhibition of the LOX enzyme family members with old and new ligands. Selectivity analysis revisited.,  28  (18): [PMID:30098867] [10.1016/j.bmcl.2018.07.001]

2. Dechering K; Duffey M.  (2022)  Replenishing the malaria drug discovery pipeline: Screening and hit evaluation of the MMV Hit Generation Library 1 (HGL1) against asexual blood stage Plasmodium falciparum ,using a nano luciferase reporter read-out,  [10.6019/CHEMBL4888484]

Source

Source(2):

• Scientific Literature
• MMV Malaria HGL