US8476255, 57

ID: ALA3647936

PubChem CID: 25263650

Max Phase: Preclinical

Molecular Formula: C25H24N2O4S

Molecular Weight: 448.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C(=C\c2ccc(SC)cc2)C(=O)NCc2ccc(C(=O)NO)cc2)cc1

Standard InChI:  InChI=1S/C25H24N2O4S/c1-31-21-11-9-19(10-12-21)23(15-17-5-13-22(32-2)14-6-17)25(29)26-16-18-3-7-20(8-4-18)24(28)27-30/h3-15,30H,16H2,1-2H3,(H,26,29)(H,27,28)/b23-15+

Standard InChI Key:  GONUDRZNKYWMTF-HZHRSRAPSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    2.5956   -2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5998    1.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8983    0.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967   -0.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1934   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1888   -3.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8875   -3.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798   -5.2557    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378   -5.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5907   -3.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953   -1.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6013    2.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6414    3.5980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3028    3.7520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3044    5.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0059    6.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052    7.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941    8.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5928    7.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5923    6.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2930    5.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8944    8.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969    9.4518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1928    7.4990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2335    8.0965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18 11  1  0
  9 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3647936

   N-hydroxy-4-[[[(E)-2-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-enoyl]amino]methyl]benzamide

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: 448.54

Molecular Weight (Monoisotopic): 448.1457

AlogP: 4.39

#Rotatable Bonds: 8

Polar Surface Area: 87.66

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.05

CX Basic pKa: ┄

CX LogP: 4.26

CX LogD: 4.25

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.16

Np Likeness Score: -0.84

References

1.  (2013)  Histone deacetylase inhibitors, 

Source

Source(1):

• BindingDB Database