4-(2-naphthamido)phenyl 4-fluorobenzenesulfonate

ID: ALA4554380

PubChem CID: 155556622

Max Phase: Preclinical

Molecular Formula: C23H16FNO4S

Molecular Weight: 421.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(OS(=O)(=O)c2ccc(F)cc2)cc1)c1ccc2ccccc2c1

Standard InChI:  InChI=1S/C23H16FNO4S/c24-19-7-13-22(14-8-19)30(27,28)29-21-11-9-20(10-12-21)25-23(26)18-6-5-16-3-1-2-4-17(16)15-18/h1-15H,(H,25,26)

Standard InChI Key:  IQXLISNWIFXQAO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   21.4988  -22.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4977  -22.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2057  -23.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2039  -21.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9126  -22.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9133  -22.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7218  -23.4261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1345  -24.1360    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.5430  -23.4237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5529  -23.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5518  -24.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2598  -24.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9695  -24.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9666  -23.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2580  -22.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6728  -22.9039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3820  -23.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0882  -22.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3851  -24.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8437  -24.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4283  -24.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7215  -24.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0158  -24.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0166  -25.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7291  -25.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4319  -25.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7958  -23.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7846  -21.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0819  -22.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3101  -25.7724    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  8  7  2  0
  9  8  2  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 11 20  1  0
 20  8  1  0
  8 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 18 27  2  0
 27  2  1  0
  1 28  1  0
 28 29  2  0
 29 18  1  0
 24 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554380

   ---

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: 421.45

Molecular Weight (Monoisotopic): 421.0784

AlogP: 5.00

#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: 5.41

CX LogD: 5.41

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -1.29

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