4-(4-chlorobenzamido)phenyl 4-fluorobenzenesulfonate

ID: ALA4528958

PubChem CID: 32937654

Max Phase: Preclinical

Molecular Formula: C19H13ClFNO4S

Molecular Weight: 405.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(OS(=O)(=O)c2ccc(F)cc2)cc1)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C19H13ClFNO4S/c20-14-3-1-13(2-4-14)19(23)22-16-7-9-17(10-8-16)26-27(24,25)18-11-5-15(21)6-12-18/h1-12H,(H,22,23)

Standard InChI Key:  SJBSFUZVXIXXPQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   37.1863   -9.6866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5991  -10.3965    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   38.0075   -9.6841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0174   -9.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0163  -10.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7243  -10.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4340  -10.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4311   -9.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7225   -9.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1373   -9.1644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.8465   -9.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5527   -9.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8496  -10.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3082  -10.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8928  -10.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1860  -10.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4803  -10.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4811  -11.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1936  -12.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8964  -11.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2603   -9.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9659   -9.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9633   -8.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2491   -7.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5464   -8.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6689   -7.9276    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.7746  -12.0328    0.0000 F   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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  0
 14  2  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 12 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
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 23 26  1  0
 18 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4528958

   [4-[(4-Chlorobenzoyl)amino]phenyl] 4-fluorobenzenesulfonate

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: 405.83

Molecular Weight (Monoisotopic): 405.0238

AlogP: 4.50

#Rotatable Bonds: 5

Polar Surface Area: 72.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.03

CX LogD: 5.03

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -1.57

References

1. Semreen MH, El-Gamal MI, Ullah S, Jalil S, Zaib S, Anbar HS, Lecka J, Sévigny J, Iqbal J..  (2019)  Synthesis, biological evaluation, and molecular docking study of sulfonate derivatives as nucleotide pyrophosphatase/phosphodiesterase (NPP) inhibitors.,  27  (13): [PMID:31088715] [10.1016/j.bmc.2019.04.031]

2. Nadel, Yael Y and 11 more authors.  2014-06-12  Highly potent and selective ectonucleotide pyrophosphatase/phosphodiesterase I inhibitors based on an adenosine 5'-(α or γ)-thio-(α,β- or β,γ)-methylenetriphosphate scaffold.  [PMID:24846781]

3. Lee, Sang-Yong SY and 5 more authors.  2016-07-15  Thiazolo[3,2-a]benzimidazol-3(2H)-one derivatives: Structure-activity relationships of selective nucleotide pyrophosphatase/phosphodiesterase1 (NPP1) inhibitors.  [PMID:27265686]

4. Zelikman, Vadim V and 8 more authors.  2018-05-10  Highly Selective and Potent Ectonucleotide Pyrophosphatase-1 (NPP1) Inhibitors Based on Uridine 5'-Pα,α-Dithiophosphate Analogues.  [PMID:29681152]

5. Nassir, Molhm and 8 more authors.  2019-12-15  Structure-activity relationship study of NPP1 inhibitors based on uracil-N1-(methoxy)ethyl-β-phosphate scaffold.  [PMID:31610377]

6. Ahmad, Haseen and 7 more authors.  2020-12-15  Synthesis of biphenyl oxazole derivatives via Suzuki coupling and biological evaluations as nucleotide pyrophosphatase/phosphodiesterase-1 and -3 inhibitors.  [PMID:32883636]

Source

Source(1):

• Scientific Literature