N-(2-(cyclohexylamino)-2-oxoethyl)-N-(4-(hydroxycarbamoyl)benzyl)-3,5-dimethylbenzamide

ID: ALA4173361

PubChem CID: 132515050

Max Phase: Preclinical

Molecular Formula: C25H31N3O4

Molecular Weight: 437.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)cc(C(=O)N(CC(=O)NC2CCCCC2)Cc2ccc(C(=O)NO)cc2)c1

Standard InChI:  InChI=1S/C25H31N3O4/c1-17-12-18(2)14-21(13-17)25(31)28(16-23(29)26-22-6-4-3-5-7-22)15-19-8-10-20(11-9-19)24(30)27-32/h8-14,22,32H,3-7,15-16H2,1-2H3,(H,26,29)(H,27,30)

Standard InChI Key:  PEXKZGDNGWXGSQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    6.7755   -7.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7743   -8.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4824   -8.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1921   -8.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1892   -7.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4806   -7.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4782   -6.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7692   -5.8872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7668   -5.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628   -6.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3538   -5.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0652   -7.1151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3550   -5.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6469   -4.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9394   -5.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445   -5.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531   -6.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394   -6.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6448   -3.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4822   -9.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7744   -9.9739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1898   -9.9742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1896  -10.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4733   -4.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4708   -3.8422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1822   -5.0658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1773   -3.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8838   -3.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5881   -3.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5899   -2.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8811   -2.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1706   -2.6159    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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 11  1  0
 16 18  1  0
 14 19  1  0
  3 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
  9 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4173361

   ---

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: 437.54

Molecular Weight (Monoisotopic): 437.2315

AlogP: 3.51

#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: 3.56

CX LogD: 3.55

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -1.35

References

1. Porter NJ, Osko JD, Diedrich D, Kurz T, Hooker JM, Hansen FK, Christianson DW..  (2018)  Histone Deacetylase 6-Selective Inhibitors and the Influence of Capping Groups on Hydroxamate-Zinc Denticity.,  61  (17): [PMID:30118224] [10.1021/acs.jmedchem.8b01013]

2. 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]

3. Reßing N, Schliehe-Diecks J, Watson PR, Sönnichsen M, Cragin AD, Schöler A, Yang J, Schäker-Hübner L, Borkhardt A, Christianson DW, Bhatia S, Hansen FK..  (2022)  Development of Fluorinated Peptoid-Based Histone Deacetylase (HDAC) Inhibitors for Therapy-Resistant Acute Leukemia.,  65  (22.0): [PMID:36351184] [10.1021/acs.jmedchem.2c01418]

Source

Source(1):

• Scientific Literature