3-(4-(N-(2-(1-ethyl-2-methyl-1H-indol-3-yl)ethyl)sulfamoyl)phenyl)-N-hydroxyacrylamide

ID: ALA3329992

PubChem CID: 118712702

Max Phase: Preclinical

Molecular Formula: C22H25N3O4S

Molecular Weight: 427.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c(C)c(CCNS(=O)(=O)c2ccc(/C=C/C(=O)NO)cc2)c2ccccc21

Standard InChI:  InChI=1S/C22H25N3O4S/c1-3-25-16(2)19(20-6-4-5-7-21(20)25)14-15-23-30(28,29)18-11-8-17(9-12-18)10-13-22(26)24-27/h4-13,23,27H,3,14-15H2,1-2H3,(H,24,26)/b13-10+

Standard InChI Key:  RBNHUVFJQYAQNY-JLHYYAGUSA-N

Molfile:  

     RDKit          2D

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   10.0483   -7.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7574   -7.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0457   -6.7004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3367   -6.2940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6329   -7.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9265   -7.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2032   -9.8517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7988   -9.1459    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3898   -9.8491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207   -8.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8725   -9.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9644   -8.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653   -7.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2209   -8.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6708   -9.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0786  -10.1239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8808   -9.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9687   -9.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867  -10.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775   -8.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3841   -9.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0929   -8.7381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083   -8.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2136   -9.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9220   -8.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2131   -7.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5076   -7.9276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442  -10.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312  -10.9527    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
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 15 13  1  0
 13 14  2  0
 14 11  1  0
 15 16  2  0
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 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
 17 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3329992

   ---

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: 427.53

Molecular Weight (Monoisotopic): 427.1566

AlogP: 3.01

#Rotatable Bonds: 8

Polar Surface Area: 100.43

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.47

CX Basic pKa: ┄

CX LogP: 3.05

CX LogD: 3.04

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.29

Np Likeness Score: -0.97

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