3-{4-[2-(1,2-Dimethyl-1H-indol-3-yl)-ethyl-N-tertbutoxycarbonylsulfamoyl]-phenyl}-N-hydroxy-acrylamide

ID: ALA3329990

PubChem CID: 118712700

Max Phase: Preclinical

Molecular Formula: C21H23N3O4S

Molecular Weight: 413.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CCNS(=O)(=O)c2ccc(/C=C/C(=O)NO)cc2)c2ccccc2n1C

Standard InChI:  InChI=1S/C21H23N3O4S/c1-15-18(19-5-3-4-6-20(19)24(15)2)13-14-22-29(27,28)17-10-7-16(8-11-17)9-12-21(25)23-26/h3-12,22,26H,13-14H2,1-2H3,(H,23,25)/b12-9+

Standard InChI Key:  HBBFWMSCYPNIJW-FMIVXFBMSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    9.3419   -7.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   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
  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
 17 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3329990

   ---

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: 413.50

Molecular Weight (Monoisotopic): 413.1409

AlogP: 2.53

#Rotatable Bonds: 7

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: 2.69

CX LogD: 2.69

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.31

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]

Source

Source(1):

• Scientific Literature