N-(2-(cyclohexylamino)-2-oxoethyl)-N-(4-(hydroxycarbamoyl)benzyl)-3-methylbenzamide

ID: ALA4278144

PubChem CID: 145981616

Max Phase: Preclinical

Molecular Formula: C24H29N3O4

Molecular Weight: 423.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C(=O)N(CC(=O)NC2CCCCC2)Cc2ccc(C(=O)NO)cc2)c1

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

Standard InChI Key:  YXWNLMBAWUUDHO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   24.4235   -5.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4224   -6.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1304   -6.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8401   -6.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8373   -5.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1286   -5.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5484   -6.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5497   -7.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2555   -6.5784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9638   -6.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7157   -5.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0081   -5.7619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3003   -5.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3001   -4.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0077   -4.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0083   -6.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7161   -6.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3007   -6.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5944   -6.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8873   -6.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8870   -7.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5998   -8.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3040   -7.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5969   -4.1241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8840   -2.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5880   -3.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2906   -2.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2952   -2.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5911   -1.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8825   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6029   -9.0273    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
 22 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4278144

   ---

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: -1.56

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