2-[(2Z)-2-[5-oxo-1-(4-sulfamoylphenyl)pyrazol-4-ylidene]hydrazino]benzoic acid

ID: ALA5278316

Max Phase: Preclinical

Molecular Formula: C16H13N5O5S

Molecular Weight: 387.38

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(N2N=C/C(=N/Nc3ccccc3C(=O)O)C2=O)cc1

Standard InChI:  InChI=1S/C16H13N5O5S/c17-27(25,26)11-7-5-10(6-8-11)21-15(22)14(9-18-21)20-19-13-4-2-1-3-12(13)16(23)24/h1-9,19H,(H,23,24)(H2,17,25,26)/b20-14-

Standard InChI Key:  VHNWYITXUYHPTH-ZHZULCJRSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -0.5992    2.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2257    2.0913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4758    1.2873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776    0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    1.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776   -0.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6416    1.0952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    0.2985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6517    0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2725    1.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559    1.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6499    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8634    0.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2843    0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868    0.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8654   -0.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6599   -0.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2432   -0.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0323    0.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2374    0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2822   -1.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856   -1.0812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4957   -2.0913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6600    0.4331    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2432    1.0162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4466   -0.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2432   -0.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  5  4  1  0
  4  6  2  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  3 10  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 10 15  1  0
 16  9  2  0
 17 16  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
  9 20  1  0
 16 21  1  0
 21 22  2  0
 21 23  1  0
 13 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278316

   ---

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: 387.38

Molecular Weight (Monoisotopic): 387.0637

AlogP: 0.83

#Rotatable Bonds: 5

Polar Surface Area: 154.52

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.40

CX Basic pKa: ┄

CX LogP: 2.71

CX LogD: -0.80

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: -1.16

References

1. Zhao Z, Dai X, Li C, Wang X, Tian J, Feng Y, Xie J, Ma C, Nie Z, Fan P, Qian M, He X, Wu S, Zhang Y, Zheng X..  (2020)  Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect.,  186  [PMID:31761383] [10.1016/j.ejmech.2019.111893]

Source

Source(1):

• Scientific Literature