4-chloro-N-(3-(3-hydroxy-4-oxocyclopent-2-enyl)phenethyl)benzenesulfonamide

ID: ALA3326603

PubChem CID: 118711723

Max Phase: Preclinical

Molecular Formula: C19H18ClNO4S

Molecular Weight: 391.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CC(c2cccc(CCNS(=O)(=O)c3ccc(Cl)cc3)c2)C=C1O

Standard InChI:  InChI=1S/C19H18ClNO4S/c20-16-4-6-17(7-5-16)26(24,25)21-9-8-13-2-1-3-14(10-13)15-11-18(22)19(23)12-15/h1-7,10-11,15,21-22H,8-9,12H2

Standard InChI Key:  HZRKBGSHFNWQJJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    5.3860  -11.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9700  -10.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3941  -11.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8561  -11.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0933  -11.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1660  -10.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5439  -10.0485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6727  -11.0960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2439  -11.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1032  -11.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5298  -10.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1059  -12.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8169  -11.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8151   -9.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5287  -11.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8038  -12.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3887  -11.5057    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.2446   -9.8478    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8269  -12.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0987  -10.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9790  -12.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9599  -11.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5362  -12.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1016  -11.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5311  -11.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8156  -11.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
  5  1  1  0
  5  6  1  0
  6  2  1  0
  6  7  2  0
  2  3  1  0
  3  4  1  0
 11 18  1  0
 12 19  1  0
 14 20  2  0
 24 17  1  0
 15 11  2  0
 17  8  1  0
 17 16  2  0
 19 23  2  0
 10 12  2  0
 24 13  2  0
 21 17  2  0
 11 14  1  0
 20 24  1  0
 22  9  1  0
 23 25  1  0
 26 10  1  0
 13 15  1  0
 25 26  2  0
  9 25  1  0
  8 22  1  0
 10  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3326603

   ---

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: 391.88

Molecular Weight (Monoisotopic): 391.0645

AlogP: 3.36

#Rotatable Bonds: 6

Polar Surface Area: 83.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.96

CX Basic pKa: ┄

CX LogP: 3.39

CX LogD: 3.38

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: -0.42

References

1. Ballatore C, Gay B, Huang L, Robinson KH, James MJ, Trojanowski JQ, Lee VM, Brunden KR, Smith AB..  (2014)  Evaluation of the cyclopentane-1,2-dione as a potential bio-isostere of the carboxylic acid functional group.,  24  (17): [PMID:25127105] [10.1016/j.bmcl.2014.07.047]

Source

Source(1):

• Scientific Literature