(E)-3-(3-((((6-bromoquinolin-2-yl)methyl)amino)methyl)phenyl)-N-hydroxyacrylamide

ID: ALA4099070

PubChem CID: 137662080

Max Phase: Preclinical

Molecular Formula: C20H18BrN3O2

Molecular Weight: 412.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cccc(CNCc2ccc3cc(Br)ccc3n2)c1)NO

Standard InChI:  InChI=1S/C20H18BrN3O2/c21-17-6-8-19-16(11-17)5-7-18(23-19)13-22-12-15-3-1-2-14(10-15)4-9-20(25)24-26/h1-11,22,26H,12-13H2,(H,24,25)/b9-4+

Standard InChI Key:  WSKYPLJHHVNQSP-RUDMXATFSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   37.4573  -11.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4562  -11.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1642  -12.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1624  -10.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8710  -11.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8718  -11.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5803  -12.2339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.2886  -11.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2839  -11.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5748  -10.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9979  -12.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7040  -11.8176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.4133  -12.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1194  -11.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8236  -12.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5293  -11.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5265  -10.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8122  -10.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1095  -10.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7495  -10.6030    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   45.2383  -12.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9447  -11.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.6538  -12.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.3601  -11.8005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   46.6565  -13.0287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   48.0692  -12.2067    0.0000 O   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
  1 20  1  0
 16 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099070

   ---

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: 412.29

Molecular Weight (Monoisotopic): 411.0582

AlogP: 3.81

#Rotatable Bonds: 6

Polar Surface Area: 74.25

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.56

CX Basic pKa: 7.85

CX LogP: 3.48

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.33

Np Likeness Score: -0.73

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