4-(cyclopentanecarboxamido)phenyl 4-fluorobenzenesulfonate

ID: ALA4538105

PubChem CID: 155549452

Max Phase: Preclinical

Molecular Formula: C18H18FNO4S

Molecular Weight: 363.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(OS(=O)(=O)c2ccc(F)cc2)cc1)C1CCCC1

Standard InChI:  InChI=1S/C18H18FNO4S/c19-14-5-11-17(12-6-14)25(22,23)24-16-9-7-15(8-10-16)20-18(21)13-3-1-2-4-13/h5-13H,1-4H2,(H,20,21)

Standard InChI Key:  IPTALSQODYZAMP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   31.8581   -2.6208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2708   -3.3307    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.6792   -2.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6891   -2.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6880   -3.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3960   -3.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1057   -3.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1029   -2.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3943   -2.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8090   -2.0986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5183   -2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2245   -2.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5214   -3.3217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9800   -3.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5646   -3.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8578   -3.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1520   -3.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1529   -4.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8654   -4.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5682   -4.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9952   -2.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4899   -1.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0240   -1.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2416   -1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4463   -4.9670    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  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 12  1  0
 18 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538105

   ---

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: 363.41

Molecular Weight (Monoisotopic): 363.0941

AlogP: 3.72

#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: 4.24

CX LogD: 4.24

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: -1.55

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