(E)-4-(3-(hydroxyamino)-3-oxoprop-1-en-1-yl)-N-((8-methoxyquinolin-2-yl)methyl)-N-phenylbenzamide

ID: ALA4087984

PubChem CID: 137645100

Max Phase: Preclinical

Molecular Formula: C27H23N3O4

Molecular Weight: 453.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc2ccc(CN(C(=O)c3ccc(/C=C/C(=O)NO)cc3)c3ccccc3)nc12

Standard InChI:  InChI=1S/C27H23N3O4/c1-34-24-9-5-6-20-15-16-22(28-26(20)24)18-30(23-7-3-2-4-8-23)27(32)21-13-10-19(11-14-21)12-17-25(31)29-33/h2-17,33H,18H2,1H3,(H,29,31)/b17-12+

Standard InChI Key:  XQZKZVIFDHWYMG-SFQUDFHCSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   36.2439  -20.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2428  -21.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9508  -22.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9490  -20.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6576  -20.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6584  -21.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3669  -22.0773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.0752  -21.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0705  -20.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3613  -20.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7845  -22.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4906  -21.6610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.1999  -22.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9060  -21.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6102  -22.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3158  -21.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3131  -20.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5988  -20.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8961  -20.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0187  -20.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7285  -20.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4341  -20.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1439  -20.8207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.4298  -19.5986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.1482  -21.6379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4840  -20.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1918  -20.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1856  -19.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4729  -19.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7650  -19.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7748  -20.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2031  -22.8840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9527  -22.9005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2459  -23.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 12 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
 13 32  2  0
  3 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087984

   ---

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: 453.50

Molecular Weight (Monoisotopic): 453.1689

AlogP: 4.61

#Rotatable Bonds: 7

Polar Surface Area: 91.76

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.56

CX Basic pKa: 1.91

CX LogP: 4.09

CX LogD: 4.08

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.24

Np Likeness Score: -0.96

References

1. Chen C, Hou X, Wang G, Pan W, Yang X, Zhang Y, Fang H..  (2017)  Design, synthesis and biological evaluation of quinoline derivatives as HDAC class I inhibitors.,  133  [PMID:28371677] [10.1016/j.ejmech.2017.03.064]

Source

Source(1):

• Scientific Literature