N-hydroxy-3-{3-[2-(2-methyl-1H-indol-3-yl)-ethylsulfamoyl]-phenyl}-acrylamide

ID: ALA3329993

PubChem CID: 118712703

Max Phase: Preclinical

Molecular Formula: C20H21N3O4S

Molecular Weight: 399.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2ccccc2c1CCNS(=O)(=O)c1cccc(/C=C/C(=O)NO)c1

Standard InChI:  InChI=1S/C20H21N3O4S/c1-14-17(18-7-2-3-8-19(18)22-14)11-12-21-28(26,27)16-6-4-5-15(13-16)9-10-20(24)23-25/h2-10,13,21-22,25H,11-12H2,1H3,(H,23,24)/b10-9+

Standard InChI Key:  PDNOQCXGBAEPEF-MDZDMXLPSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    6.3807   -3.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762   -3.1656    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5673   -3.8687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7982   -2.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -3.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418   -2.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3427   -1.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3984   -2.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8483   -3.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2561   -4.1436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0583   -3.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1461   -3.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6641   -4.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550   -2.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5615   -3.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -2.7578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6858   -2.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3911   -3.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0994   -2.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1021   -1.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3906   -1.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6851   -1.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8058   -3.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5148   -2.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2212   -3.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9302   -2.7765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2186   -4.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5096   -4.4063    0.0000 O   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  9  1  0
  8  6  1  0
  6  7  2  0
  7  4  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 11 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
  2 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 19 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3329993

   ---

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: 399.47

Molecular Weight (Monoisotopic): 399.1253

AlogP: 2.52

#Rotatable Bonds: 7

Polar Surface Area: 111.29

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.45

CX Basic pKa: ┄

CX LogP: 2.47

CX LogD: 2.46

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.28

Np Likeness Score: -0.89

References

1. Mehndiratta S, Hsieh YL, Liu YM, Wang AW, Lee HY, Liang LY, Kumar S, Teng CM, Yang CR, Liou JP..  (2014)  Indole-3-ethylsulfamoylphenylacrylamides: potent histone deacetylase inhibitors with anti-inflammatory activity.,  85  [PMID:25113875] [10.1016/j.ejmech.2014.08.020]

Source

Source(1):

• Scientific Literature