(E)-2-(2-(4-Chlorophenyl)hydrazineylidene)-3-oxo-N-(4-sulfamoylphenyl)butanamide

ID: ALA4483065

PubChem CID: 155539730

Max Phase: Preclinical

Molecular Formula: C16H15ClN4O4S

Molecular Weight: 394.84

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)/C(=N\Nc1ccc(Cl)cc1)C(=O)Nc1ccc(S(N)(=O)=O)cc1

Standard InChI:  InChI=1S/C16H15ClN4O4S/c1-10(22)15(21-20-13-4-2-11(17)3-5-13)16(23)19-12-6-8-14(9-7-12)26(18,24)25/h2-9,20H,1H3,(H,19,23)(H2,18,24,25)/b21-15+

Standard InChI Key:  YQYPJWHEQVOQDW-RCCKNPSSSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   15.0355  -25.5145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4482  -26.2244    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.8566  -25.5120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1567  -26.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1555  -27.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8636  -27.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5732  -27.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5704  -26.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8618  -26.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7413  -26.6333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2816  -27.8595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9887  -27.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6970  -27.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9874  -26.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4041  -27.4476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1124  -27.8551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8195  -27.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6983  -28.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9912  -29.0842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4066  -29.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5250  -27.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2316  -27.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2307  -26.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5174  -26.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8138  -26.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9373  -26.2153    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  4  2  1  0
  2 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 13 18  1  0
 18 19  2  0
 18 20  1  0
 17 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 17  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483065

   ---

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: 394.84

Molecular Weight (Monoisotopic): 394.0503

AlogP: 1.98

#Rotatable Bonds: 6

Polar Surface Area: 130.72

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.52

CX Basic pKa: ┄

CX LogP: 3.11

CX LogD: 1.40

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.39

Np Likeness Score: -1.51

References

1. Fares M, Eldehna WM, Bua S, Lanzi C, Lucarini L, Masini E, Peat TS, Abdel-Aziz HA, Nocentini A, Keller PA, Supuran CT..  (2020)  Discovery of Potent Dual-Tailed Benzenesulfonamide Inhibitors of Human Carbonic Anhydrases Implicated in Glaucoma and in Vivo Profiling of Their Intraocular Pressure-Lowering Action.,  63  (6): [PMID:32031797] [10.1021/acs.jmedchem.9b02090]

Source

Source(1):

• Scientific Literature