4-(cyclohexanecarboxamido)phenyl propane-1-sulfonate

ID: ALA4522503

PubChem CID: 155543015

Max Phase: Preclinical

Molecular Formula: C16H23NO4S

Molecular Weight: 325.43

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H23NO4S/c1-2-12-22(19,20)21-15-10-8-14(9-11-15)17-16(18)13-6-4-3-5-7-13/h8-11,13H,2-7,12H2,1H3,(H,17,18)

Standard InChI Key:  BEDTUCIEQCFUOG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   31.3587   -8.9437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7714   -9.6536    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.1798   -8.9412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1898   -8.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1886   -9.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8967  -10.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6063   -9.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6035   -8.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8949   -8.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3096   -8.4215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0189   -8.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7251   -8.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0220   -9.6446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4806  -10.0639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0652  -10.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4331   -8.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1372   -8.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1383   -7.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4291   -7.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7188   -7.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3568   -9.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6497  -10.0650    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
 15 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4522503

   ---

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: 325.43

Molecular Weight (Monoisotopic): 325.1348

AlogP: 3.32

#Rotatable Bonds: 6

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: 3.46

CX LogD: 3.46

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: -1.38

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