(S,Z)-N-(1-bromo-3-((1-hydroxy-3-phenylpropan-2-yl)amino)-3-oxo-1-phenylprop-1-en-2-yl)-2,4-dichlorobenzamide

ID: ALA4742126

PubChem CID: 162647307

Max Phase: Preclinical

Molecular Formula: C25H21BrCl2N2O3

Molecular Weight: 548.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(N[C@H](CO)Cc1ccccc1)/C(NC(=O)c1ccc(Cl)cc1Cl)=C(/Br)c1ccccc1

Standard InChI:  InChI=1S/C25H21BrCl2N2O3/c26-22(17-9-5-2-6-10-17)23(30-24(32)20-12-11-18(27)14-21(20)28)25(33)29-19(15-31)13-16-7-3-1-4-8-16/h1-12,14,19,31H,13,15H2,(H,29,33)(H,30,32)/b23-22-/t19-/m0/s1

Standard InChI Key:  TYYFELSMWVVDKL-ZABCRHKISA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   13.9239   -8.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9227   -9.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6308  -10.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3404   -9.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3376   -8.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6290   -8.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6306  -11.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9227  -11.4225    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.3382  -11.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3380  -12.2401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0460  -11.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7536  -11.4232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0462  -10.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4614  -11.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1690  -11.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4616  -10.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1694   -9.7892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1688  -12.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0456  -12.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0454  -13.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7534  -12.2404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3385  -13.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3380  -14.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0461  -15.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7563  -14.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7533  -13.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4614  -12.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4608  -13.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1690  -13.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8791  -13.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8762  -12.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6314  -13.4627    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.0470  -15.9154    0.0000 Cl  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
  3  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 14 12  1  6
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 15 18  1  0
 10 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 20  1  0
 18 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 18  1  0
 22 32  1  0
 24 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4742126

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 548.26

Molecular Weight (Monoisotopic): 546.0113

AlogP: 5.21

#Rotatable Bonds: 8

Polar Surface Area: 78.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.13

CX Basic pKa: ┄

CX LogP: 4.98

CX LogD: 4.98

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: -0.73

References

1. Gu X,Zhang Y,Zou Y,Li X,Guan M,Zhou Q,Qiu J.  (2021)  Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents.,  29  [PMID:33285406] [10.1016/j.bmc.2020.115892]

Source

Source(1):

• Scientific Literature