4-(2-naphthamido)phenyl benzenesulfonate

ID: ALA4575963

PubChem CID: 155564260

Max Phase: Preclinical

Molecular Formula: C23H17NO4S

Molecular Weight: 403.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(OS(=O)(=O)c2ccccc2)cc1)c1ccc2ccccc2c1

Standard InChI:  InChI=1S/C23H17NO4S/c25-23(19-11-10-17-6-4-5-7-18(17)16-19)24-20-12-14-21(15-13-20)28-29(26,27)22-8-2-1-3-9-22/h1-16H,(H,24,25)

Standard InChI Key:  WJAZEJBEXRUXAC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   20.8797  -15.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8786  -15.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5866  -16.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5848  -14.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2935  -15.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2942  -15.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1027  -16.4883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5155  -17.1982    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.9239  -16.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9338  -16.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9327  -17.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6407  -17.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3504  -17.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3475  -16.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6389  -15.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0537  -15.9661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7630  -16.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4691  -15.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7660  -17.1892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2246  -17.6085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8092  -17.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1024  -17.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3967  -17.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3975  -18.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1100  -18.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8129  -18.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1767  -16.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1656  -14.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4628  -15.1486    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA4575963

   ---

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: 403.46

Molecular Weight (Monoisotopic): 403.0878

AlogP: 4.86

#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: 5.27

CX LogD: 5.27

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -1.06

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