4-(2-(2-Ethoxyphenyl)hydrazono)-1-(3-hydroxy-5-(thiophen-2-yl)phenyl)-3-methyl-1H-pyrazol-5(4H)-one

ID: ALA3417405

PubChem CID: 136934826

Max Phase: Preclinical

Molecular Formula: C22H20N4O3S

Molecular Weight: 420.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccccc1N/N=C1\C(=O)N(c2cc(O)cc(-c3cccs3)c2)N=C1C

Standard InChI:  InChI=1S/C22H20N4O3S/c1-3-29-19-8-5-4-7-18(19)23-24-21-14(2)25-26(22(21)28)16-11-15(12-17(27)13-16)20-9-6-10-30-20/h4-13,23,27H,3H2,1-2H3/b24-21-

Standard InChI Key:  YUPUDWSGAPMILZ-FLFQWRMESA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9492    0.8772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9546    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2067    3.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7390    2.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8437    3.7801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1478    1.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8154    4.6596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9334    5.8739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5432    7.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0353    7.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6475    8.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7677    9.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2757    9.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6635    8.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1703    8.3088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918    9.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979    9.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511    0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9530    1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010    3.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7342    2.9815    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  4  8  1  0
 12 13  2  0
 10 14  1  0
 11 15  2  0
 15 16  1  0
 16 17  1  0
  2 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 18 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3417405

   ---

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: 420.49

Molecular Weight (Monoisotopic): 420.1256

AlogP: 4.71

#Rotatable Bonds: 6

Polar Surface Area: 86.52

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.41

CX Basic pKa: ┄

CX LogP: 5.32

CX LogD: 3.74

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: -1.49

References

1. Stornaiuolo M, La Regina G, Passacantilli S, Grassia G, Coluccia A, La Pietra V, Giustiniano M, Cassese H, Di Maro S, Brancaccio D, Taliani S, Ialenti A, Silvestri R, Martini C, Novellino E, Marinelli L..  (2015)  Structure-based lead optimization and biological evaluation of BAX direct activators as novel potential anticancer agents.,  58  (5): [PMID:25668341] [10.1021/jm501123r]

Source

Source(1):

• Scientific Literature