N-hydroxy-3-(2-phenethyl-1-(2-(piperidin-1-yl)ethyl)-1H-benzo[d]imidazol-5-yl)acrylamide dihydrochloride

ID: ALA3216905

PubChem CID: 90665048

Max Phase: Preclinical

Molecular Formula: C25H32Cl2N4O2

Molecular Weight: 418.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.O=C(/C=C/c1ccc2c(c1)nc(CCc1ccccc1)n2CCN1CCCCC1)NO

Standard InChI:  InChI=1S/C25H30N4O2.2ClH/c30-25(27-31)14-11-21-9-12-23-22(19-21)26-24(13-10-20-7-3-1-4-8-20)29(23)18-17-28-15-5-2-6-16-28;;/h1,3-4,7-9,11-12,14,19,31H,2,5-6,10,13,15-18H2,(H,27,30);2*1H/b14-11+;;

Standard InChI Key:  RLDKZHWPSMUDLF-IVKCLRODSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
   11.8512    2.1243    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217   -1.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153   -0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2216   -1.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5151   -0.7033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2318   -2.6643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5596   -1.2941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -1.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3513   -1.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1161   -2.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6160   -2.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3512   -1.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5865    0.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0866    0.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1182    4.3614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5858    4.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0509    6.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    7.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5808    6.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1158    5.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3512    2.1243    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 14 16  1  0
  4  5  2  0
  9 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 18 19  1  0
  9 10  1  0
 19 20  2  0
 10  6  1  0
 20 21  1  0
  5  7  1  0
 21 22  2  0
  4 11  1  0
 22 23  1  0
  6  7  2  0
 23 24  2  0
 24 19  1  0
 11 12  2  0
 10 25  1  0
  2  3  2  0
 25 26  1  0
 12 13  1  0
 26 27  1  0
 27 28  1  0
  6  2  1  0
 13 14  1  0
  3  4  1  0
 13 15  2  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

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: 418.54

Molecular Weight (Monoisotopic): 418.2369

AlogP: 3.83

#Rotatable Bonds: 8

Polar Surface Area: 70.39

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.70

CX Basic pKa: 9.01

CX LogP: 3.62

CX LogD: 2.35

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.33

Np Likeness Score: -1.03

References

1. Wang H, Yu N, Song H, Chen D, Zou Y, Deng W, Lye PL, Chang J, Ng M, Sun ET, Sangthongpitag K, Wang X, Wu X, Khng HH, Fang L, Goh SK, Ong WC, Bonday Z, Stünkel W, Poulsen A, Entzeroth M..  (2009)  N-Hydroxy-1,2-disubstituted-1H-benzimidazol-5-yl acrylamides as novel histone deacetylase inhibitors: design, synthesis, SAR studies, and in vivo antitumor activity.,  19  (5): [PMID:19181524] [10.1016/j.bmcl.2009.01.041]

Source

Source(1):

• Scientific Literature