N-hydroxy-3-{4-[2-(2-methyl-1H-indol-3-yl)-ethylsulfamoyl]-phenyl}-acrylamide

ID: ALA3329991

PubChem CID: 118712701

Max Phase: Preclinical

Molecular Formula: C20H21N3O4S

Molecular Weight: 399.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2ccccc2c1CCNS(=O)(=O)c1ccc(/C=C/C(=O)NO)cc1

Standard InChI:  InChI=1S/C20H21N3O4S/c1-14-17(18-4-2-3-5-19(18)22-14)12-13-21-28(26,27)16-9-6-15(7-10-16)8-11-20(24)23-25/h2-11,21-22,25H,12-13H2,1H3,(H,23,24)/b11-8+

Standard InChI Key:  JMDMVJXTEMLGRO-DHZHZOJOSA-N

Molfile:  

     RDKit          2D

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    8.7187   -7.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4251   -7.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1341   -7.7794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4225   -6.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7135   -6.1496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0097   -7.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3033   -7.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5800   -9.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1755   -9.0015    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7666   -9.7046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -8.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2493   -9.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3412   -7.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5421   -7.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5977   -8.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0476   -9.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -9.9795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -9.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455   -8.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8634  -10.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0543   -8.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7609   -9.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4697   -8.5937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8851   -8.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5904   -9.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2987   -8.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5899   -7.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844   -7.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  1  6  2  0
  6  7  1  0
  9  8  2  0
 10  9  2  0
 11 12  2  0
 12 16  1  0
 15 13  1  0
 13 14  2  0
 14 11  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 18 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23  9  1  0
  9 24  1  0
 24 25  2  0
 25 26  1  0
 26  7  2  0
  7 27  1  0
 27 28  2  0
 28 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3329991

   ---

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: 9.47

CX Basic pKa: ┄

CX LogP: 2.47

CX LogD: 2.46

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.28

Np Likeness Score: -0.83

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]

2. Liu W, Liang Y, Si X..  (2020)  Hydroxamic acid hybrids as the potential anticancer agents: An Overview.,  205  [PMID:32791404] [10.1016/j.ejmech.2020.112679]

Source

Source(1):

• Scientific Literature