N-(2-(cyclohexylamino)-2-oxoethyl)-4-(dimethylamino)-N-(4-(hydroxycarbamoyl)benzyl)benzamide

ID: ALA4063658

PubChem CID: 132515052

Max Phase: Preclinical

Molecular Formula: C25H32N4O4

Molecular Weight: 452.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(C(=O)N(CC(=O)NC2CCCCC2)Cc2ccc(C(=O)NO)cc2)cc1

Standard InChI:  InChI=1S/C25H32N4O4/c1-28(2)22-14-12-20(13-15-22)25(32)29(17-23(30)26-21-6-4-3-5-7-21)16-18-8-10-19(11-9-18)24(31)27-33/h8-15,21,33H,3-7,16-17H2,1-2H3,(H,26,30)(H,27,31)

Standard InChI Key:  FFQAZZWXNIAWGV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   28.3210   -4.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3210   -5.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0263   -5.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7316   -5.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7316   -4.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0263   -4.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0263   -6.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7340   -6.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7340   -7.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4417   -6.5251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4417   -8.1595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4417   -8.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1494   -7.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8572   -8.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8553   -8.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5622   -9.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2709   -8.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2683   -8.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5608   -7.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9791   -9.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9802  -10.2025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6863   -8.9758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3946   -9.3834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1494   -9.3853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7340   -9.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0275   -8.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3203   -9.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3198  -10.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0325  -10.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7368  -10.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6127  -10.6080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9044  -10.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6138  -11.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 12 24  2  0
 12 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 31 32  1  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063658

   ---

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: 452.56

Molecular Weight (Monoisotopic): 452.2424

AlogP: 2.96

#Rotatable Bonds: 8

Polar Surface Area: 101.98

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.05

CX Basic pKa: 3.45

CX LogP: 2.65

CX LogD: 2.64

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: -1.40

References

1. Krieger V, Hamacher A, Gertzen CGW, Senger J, Zwinderman MRH, Marek M, Romier C, Dekker FJ, Kurz T, Jung M, Gohlke H, Kassack MU, Hansen FK..  (2017)  Design, Multicomponent Synthesis, and Anticancer Activity of a Focused Histone Deacetylase (HDAC) Inhibitor Library with Peptoid-Based Cap Groups.,  60  (13): [PMID:28574690] [10.1021/acs.jmedchem.7b00197]

2. Krieger V, Hamacher A, Gertzen CGW, Senger J, Zwinderman MRH, Marek M, Romier C, Dekker FJ, Kurz T, Jung M, Gohlke H, Kassack MU, Hansen FK..  (2017)  Design, Multicomponent Synthesis, and Anticancer Activity of a Focused Histone Deacetylase (HDAC) Inhibitor Library with Peptoid-Based Cap Groups.,  60  (13): [PMID:28574690] [10.1021/acs.jmedchem.7b00197]

3. Diedrich D, Stenzel K, Hesping E, Antonova-Koch Y, Gebru T, Duffy S, Fisher G, Schöler A, Meister S, Kurz T, Avery VM, Winzeler EA, Held J, Andrews KT, Hansen FK..  (2018)  One-pot, multi-component synthesis and structure-activity relationships of peptoid-based histone deacetylase (HDAC) inhibitors targeting malaria parasites.,  158  [PMID:30245402] [10.1016/j.ejmech.2018.09.018]

4. Wang XX,Wan RZ,Liu ZP.  (2018)  Recent advances in the discovery of potent and selective HDAC6 inhibitors.,  143  [PMID:29133060] [10.1016/j.ejmech.2017.10.040]

Source

Source(1):

• Scientific Literature