N-(2-(cyclohexylamino)-2-oxoethyl)-N-(4-(hydroxycarbamoyl)benzyl)-2-methylbenzamide

ID: ALA4288819

PubChem CID: 145992110

Max Phase: Preclinical

Molecular Formula: C24H29N3O4

Molecular Weight: 423.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1C(=O)N(CC(=O)NC1CCCCC1)Cc1ccc(C(=O)NO)cc1

Standard InChI:  InChI=1S/C24H29N3O4/c1-17-7-5-6-10-21(17)24(30)27(16-22(28)25-20-8-3-2-4-9-20)15-18-11-13-19(14-12-18)23(29)26-31/h5-7,10-14,20,31H,2-4,8-9,15-16H2,1H3,(H,25,28)(H,26,29)

Standard InChI Key:  HYPFRFUBFJLNJM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   16.2846   -5.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2835   -6.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9915   -6.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7012   -6.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6984   -5.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9897   -5.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4095   -6.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4108   -7.4628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1166   -6.2359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8250   -6.6433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5768   -5.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8692   -5.4194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1614   -5.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1612   -4.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8688   -3.7850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8694   -6.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5772   -6.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1618   -6.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4555   -6.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7484   -6.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7481   -7.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4609   -7.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1651   -7.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4580   -3.7816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7451   -2.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4491   -2.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1517   -2.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1563   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4522   -1.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7436   -1.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4575   -5.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  1 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 24  1  0
 14 15  2  0
 12 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 26 24  1  0
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 19 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4288819

   ---

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: 423.51

Molecular Weight (Monoisotopic): 423.2158

AlogP: 3.21

#Rotatable Bonds: 7

Polar Surface Area: 98.74

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.05

CX Basic pKa: ┄

CX LogP: 3.05

CX LogD: 3.04

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: -1.45

References

1. 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]

Source

Source(1):

• Scientific Literature