4-(cyclohexanecarboxamido)phenyl methanesulfonate

ID: ALA4568127

PubChem CID: 155560220

Max Phase: Preclinical

Molecular Formula: C14H19NO4S

Molecular Weight: 297.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Oc1ccc(NC(=O)C2CCCCC2)cc1

Standard InChI:  InChI=1S/C14H19NO4S/c1-20(17,18)19-13-9-7-12(8-10-13)15-14(16)11-5-3-2-4-6-11/h7-11H,2-6H2,1H3,(H,15,16)

Standard InChI Key:  BWQNRIJGJGJDPS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   11.5480   -9.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9607  -10.3635    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.3691   -9.6511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3791   -9.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3779  -10.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0860  -10.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7956  -10.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7928   -9.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0842   -9.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4990   -9.1314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2082   -9.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9144   -9.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2113  -10.3545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6699  -10.7738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2545  -10.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6224   -9.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3265   -9.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3276   -8.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6184   -7.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9081   -8.3106    0.0000 C   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
 12 16  1  0
 12 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4568127

   ---

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: 297.38

Molecular Weight (Monoisotopic): 297.1035

AlogP: 2.54

#Rotatable Bonds: 4

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: 2.43

CX LogD: 2.43

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.87

Np Likeness Score: -1.33

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