N-(2-(benzylamino)-2-oxoethyl)-N-(6-(hydroxyamino)-6-oxohexyl)-3,5-dimethylbenzamide

ID: ALA4090647

PubChem CID: 137642860

Max Phase: Preclinical

Molecular Formula: C24H31N3O4

Molecular Weight: 425.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)cc(C(=O)N(CCCCCC(=O)NO)CC(=O)NCc2ccccc2)c1

Standard InChI:  InChI=1S/C24H31N3O4/c1-18-13-19(2)15-21(14-18)24(30)27(12-8-4-7-11-22(28)26-31)17-23(29)25-16-20-9-5-3-6-10-20/h3,5-6,9-10,13-15,31H,4,7-8,11-12,16-17H2,1-2H3,(H,25,29)(H,26,28)

Standard InChI Key:  OAIPADPNBXPRRA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    2.0085  -17.2848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4057  -17.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284  -16.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1914  -17.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7943  -16.5575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715  -17.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0525  -17.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4746  -18.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0712  -19.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7522  -19.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1683  -18.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455  -16.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6654  -15.8958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6427  -17.3111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4825  -15.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228  -18.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6199  -18.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4370  -18.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8342  -19.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6513  -19.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0485  -20.1809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712  -18.7657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6285  -20.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1519  -20.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837  -18.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8797  -16.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572  -17.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8537  -18.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6716  -18.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0915  -17.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6926  -16.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 10 24  1  0
  8 25  1  0
 15 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090647

   ---

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: 425.53

Molecular Weight (Monoisotopic): 425.2315

AlogP: 3.13

#Rotatable Bonds: 11

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: 8.91

CX Basic pKa: ┄

CX LogP: 3.00

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.29

Np Likeness Score: -1.10

References

1. Krieger V, Hamacher A, Gertzen CGW, Senger J, Zwinderman MRH, Marek M, Romier C, Dekker FJ, Kurz T, Jung M, Gohlke H, Kassack MU, Hansen FK..  (2017)  Design, Multicomponent Synthesis, and Anticancer Activity of a Focused Histone Deacetylase (HDAC) Inhibitor Library with Peptoid-Based Cap Groups.,  60  (13): [PMID:28574690] [10.1021/acs.jmedchem.7b00197]

Source

Source(1):

• Scientific Literature