N-(2-(tert-butylamino)-2-oxoethyl)-N-(4-(hydroxycarbamoyl)benzyl)-3,4-dimethylbenzamide

ID: ALA4289151

PubChem CID: 145987935

Max Phase: Preclinical

Molecular Formula: C23H29N3O4

Molecular Weight: 411.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)N(CC(=O)NC(C)(C)C)Cc2ccc(C(=O)NO)cc2)cc1C

Standard InChI:  InChI=1S/C23H29N3O4/c1-15-6-9-19(12-16(15)2)22(29)26(14-20(27)24-23(3,4)5)13-17-7-10-18(11-8-17)21(28)25-30/h6-12,30H,13-14H2,1-5H3,(H,24,27)(H,25,28)

Standard InChI Key:  YSKBXECDMKZLHT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    6.7425   -6.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7413   -6.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4494   -7.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1590   -6.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1562   -6.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4476   -5.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8674   -7.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8687   -8.0488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5745   -6.8219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2828   -7.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0347   -5.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3271   -6.0054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6193   -5.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191   -4.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -4.3714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3267   -4.3710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3273   -6.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0351   -7.2310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9111   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2032   -3.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6187   -3.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044   -2.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6196   -7.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133   -6.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062   -7.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2060   -8.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9187   -8.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6229   -8.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4986   -6.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -8.4550    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 15  1  0
 14 16  2  0
 12 17  1  0
 17 18  2  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 17 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
 25 29  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4289151

   ---

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: 411.50

Molecular Weight (Monoisotopic): 411.2158

AlogP: 2.98

#Rotatable Bonds: 6

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: 2.82

CX LogD: 2.81

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.50

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