4-(4-chlorobenzamido)phenyl benzenesulfonate

ID: ALA4529912

PubChem CID: 32937631

Max Phase: Preclinical

Molecular Formula: C19H14ClNO4S

Molecular Weight: 387.84

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(OS(=O)(=O)c2ccccc2)cc1)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C19H14ClNO4S/c20-15-8-6-14(7-9-15)19(22)21-16-10-12-17(13-11-16)25-26(23,24)18-4-2-1-3-5-18/h1-13H,(H,21,22)

Standard InChI Key:  FXQDESBYVHFLBI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   36.8933   -3.6031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3060   -4.3130    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.7144   -3.6006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7244   -3.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7232   -4.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4313   -4.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1409   -4.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1381   -3.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4295   -3.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8443   -3.0809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.5535   -3.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2596   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5566   -4.3040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0152   -4.7233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5998   -4.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8930   -4.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1872   -4.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1881   -5.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9006   -5.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6034   -5.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9673   -3.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6729   -3.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6703   -2.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9561   -1.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2534   -2.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3759   -1.8441    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
  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
 25 12  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4529912

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

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: 387.84

Molecular Weight (Monoisotopic): 387.0332

AlogP: 4.36

#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: 4.89

CX LogD: 4.89

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -1.37

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