2-{(1-Isobutyl-5-phenyl-1H-pyrazol-3-yl)methyl}-2,3-dihydrobenzo[d]isothiazole1,1-dioxide

ID: ALA4104298

PubChem CID: 137658283

Max Phase: Preclinical

Molecular Formula: C20H21N3O2S

Molecular Weight: 367.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)n1nc(CN2Cc3ccccc3S2(=O)=O)cc1-c1ccccc1

Standard InChI:  InChI=1S/C20H21N3O2S/c1-15(2)23-19(16-8-4-3-5-9-16)12-18(21-23)14-22-13-17-10-6-7-11-20(17)26(22,24)25/h3-12,15H,13-14H2,1-2H3

Standard InChI Key:  IEGWCSYYRBGBLG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   11.1039   -5.3859    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.5828   -6.0490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0973   -6.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3222   -6.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3288   -5.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6230   -5.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9106   -5.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9081   -6.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6139   -6.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4000   -6.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2810   -7.9745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6198   -7.4889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8760   -6.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6944   -6.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9423   -7.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6578   -7.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8163   -4.9790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7756   -4.6359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2786   -8.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5697   -9.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9851   -9.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6703   -8.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3850   -9.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0842   -8.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0642   -7.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3490   -7.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  5  6  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 11 15  1  0
 15 16  1  0
 10 13  1  0
  2 10  1  0
  1 17  2  0
  1 18  2  0
 11 19  1  0
 19 20  1  0
 19 21  1  0
 16 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4104298

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 367.47

Molecular Weight (Monoisotopic): 367.1354

AlogP: 3.84

#Rotatable Bonds: 4

Polar Surface Area: 55.20

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.91

CX Basic pKa: 1.53

CX LogP: 3.35

CX LogD: 3.35

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -1.03

References

1. Hong JR, Choi YJ, Keum G, Nam G..  (2017)  Synthesis and diabetic neuropathic pain-alleviating effects of 2N-(pyrazol-3-yl)methylbenzo[d]isothiazole-1,1-dioxide derivatives.,  25  (17): [PMID:28720324] [10.1016/j.bmc.2017.07.008]

Source

Source(1):

• Scientific Literature