4-(2-naphthamido)phenyl 4-(trifluoromethyl)benzenesulfonate

ID: ALA4476355

PubChem CID: 155538214

Max Phase: Preclinical

Molecular Formula: C24H16F3NO4S

Molecular Weight: 471.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H16F3NO4S/c25-24(26,27)19-7-13-22(14-8-19)33(30,31)32-21-11-9-20(10-12-21)28-23(29)18-6-5-16-3-1-2-4-17(16)15-18/h1-15H,(H,28,29)

Standard InChI Key:  NOVNGEGJMQBCME-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   33.4224  -21.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4212  -21.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1293  -22.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1275  -20.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8361  -21.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8369  -21.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6454  -22.4232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0581  -23.1331    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.4665  -22.4207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4765  -22.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4753  -23.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1834  -23.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8930  -23.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8902  -22.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1816  -21.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5964  -21.9010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3056  -22.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0117  -21.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3087  -23.1241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7673  -23.5435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3519  -23.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6451  -23.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9393  -23.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9402  -24.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6527  -24.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3555  -24.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7194  -22.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7082  -20.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0055  -21.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2336  -24.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5248  -24.3629    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.2360  -25.5866    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.5211  -25.1720    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
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476355

   ---

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: 471.46

Molecular Weight (Monoisotopic): 471.0752

AlogP: 5.88

#Rotatable Bonds: 5

Polar Surface Area: 72.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.15

CX LogD: 6.15

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: -1.21

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