4-(dimethylamino)-N-(4-(hydroxycarbamoyl)benzyl)-N-(2-oxo-2-(p-tolylamino)ethyl)benzamide

ID: ALA4162282

PubChem CID: 132515051

Max Phase: Preclinical

Molecular Formula: C26H28N4O4

Molecular Weight: 460.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)CN(Cc2ccc(C(=O)NO)cc2)C(=O)c2ccc(N(C)C)cc2)cc1

Standard InChI:  InChI=1S/C26H28N4O4/c1-18-4-12-22(13-5-18)27-24(31)17-30(16-19-6-8-20(9-7-19)25(32)28-34)26(33)21-10-14-23(15-11-21)29(2)3/h4-15,34H,16-17H2,1-3H3,(H,27,31)(H,28,32)

Standard InChI Key:  UEKPDDMOEDHDCS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    6.7961  -19.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7950  -20.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5030  -20.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2127  -20.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2099  -19.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5012  -18.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4988  -17.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7899  -17.5549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7874  -16.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0834  -17.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3745  -17.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0858  -18.7828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3756  -16.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6675  -16.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9600  -16.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651  -17.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6738  -17.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5028  -21.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7950  -21.6416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2104  -21.6419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2102  -22.4591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4939  -16.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4915  -15.5098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2028  -16.7335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1980  -15.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9044  -15.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6088  -15.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6106  -14.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9018  -13.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1912  -14.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2506  -16.3416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470  -15.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5446  -16.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3186  -13.8753    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
  3 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  2  0
 25 30  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 15 31  1  0
 31 32  1  0
 31 33  1  0
 28 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4162282

   ---

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: 460.53

Molecular Weight (Monoisotopic): 460.2111

AlogP: 3.46

#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: 3.38

CX LogD: 3.37

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.35

Np Likeness Score: -1.59

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]

Source

Source(1):

• Scientific Literature