4-(cyclopentanecarboxamido)phenyl 4-(trifluoromethyl)benzenesulfonate

ID: ALA4567794

PubChem CID: 155560593

Max Phase: Preclinical

Molecular Formula: C19H18F3NO4S

Molecular Weight: 413.42

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H18F3NO4S/c20-19(21,22)14-5-11-17(12-6-14)28(25,26)27-16-9-7-15(8-10-16)23-18(24)13-3-1-2-4-13/h5-13H,1-4H2,(H,23,24)

Standard InChI Key:  HUGPPWFREWMGFZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.1396   -8.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523   -9.1583    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9607   -8.4460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707   -8.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9695   -9.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6776   -9.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3872   -9.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3844   -8.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6758   -7.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0906   -7.9262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7998   -8.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5060   -7.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8029   -9.1493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2615   -9.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8461   -9.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393   -9.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -9.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4344  -10.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469  -10.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8497  -10.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2768   -8.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7714   -7.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3055   -6.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5231   -7.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7279  -10.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0190  -10.3881    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302  -11.6118    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153  -11.1972    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
 25 26  1  0
 25 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4567794

   ---

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: 413.42

Molecular Weight (Monoisotopic): 413.0909

AlogP: 4.60

#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: 4.97

CX LogD: 4.97

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.73

Np Likeness Score: -1.43

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