4-(cyclohexanecarboxamido)phenyl 4-tert-butylbenzenesulfonate

ID: ALA4476115

PubChem CID: 155538277

Max Phase: Preclinical

Molecular Formula: C23H29NO4S

Molecular Weight: 415.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(S(=O)(=O)Oc2ccc(NC(=O)C3CCCCC3)cc2)cc1

Standard InChI:  InChI=1S/C23H29NO4S/c1-23(2,3)18-9-15-21(16-10-18)29(26,27)28-20-13-11-19(12-14-20)24-22(25)17-7-5-4-6-8-17/h9-17H,4-8H2,1-3H3,(H,24,25)

Standard InChI Key:  MLNYLAOHNCLUQX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   13.7684  -13.8675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1812  -14.5774    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.5896  -13.8650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5995  -13.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5984  -14.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3064  -14.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0161  -14.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0132  -13.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3046  -13.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7194  -13.3453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4286  -13.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1349  -13.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4317  -14.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8903  -14.9877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4749  -14.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7681  -14.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0624  -14.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0632  -15.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7757  -16.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4786  -15.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8429  -13.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5470  -13.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5481  -12.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8389  -12.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1286  -12.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3567  -16.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6478  -15.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3591  -17.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6441  -16.6162    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
 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
 12 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 18 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476115

   ---

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: 415.56

Molecular Weight (Monoisotopic): 415.1817

AlogP: 5.27

#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: 6.09

CX LogD: 6.09

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -1.29

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