2-(4-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)ethoxy)benzylidene)malononitrile

ID: ALA2296209

PubChem CID: 76316650

Max Phase: Preclinical

Molecular Formula: C20H13ClN4O2S

Molecular Weight: 408.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CC(C#N)=Cc1ccc(OCCSc2nnc(-c3ccc(Cl)cc3)o2)cc1

Standard InChI:  InChI=1S/C20H13ClN4O2S/c21-17-5-3-16(4-6-17)19-24-25-20(27-19)28-10-9-26-18-7-1-14(2-8-18)11-15(12-22)13-23/h1-8,11H,9-10H2

Standard InChI Key:  TWTBJXYZGZIUTB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.7527  -15.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1596  -14.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7523  -13.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9337  -13.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5305  -14.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768  -14.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4562  -15.0499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2344  -14.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2333  -13.9791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4545  -13.7287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9502  -15.1916    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6497  -14.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6336  -13.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3332  -13.5298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0488  -13.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0595  -14.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7742  -15.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4748  -14.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4560  -13.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7407  -13.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1909  -15.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8899  -14.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6060  -15.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8727  -13.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8588  -13.0519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3188  -15.4690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7133  -14.3956    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
  8  9  1  0
  7  8  1  0
  9 10  2  0
 10 11  1  0
 11  7  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  3  0
 24 27  3  0
  6 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296209

   2-[[4-[2-[[5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]ethoxy]phenyl]methylidene]propanedinitrile

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: 408.87

Molecular Weight (Monoisotopic): 408.0448

AlogP: 4.99

#Rotatable Bonds: 7

Polar Surface Area: 95.73

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.48

CX LogD: 4.48

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.31

Np Likeness Score: -1.89

References

1. Deora GS, Karthikeyan C, Moorthy NSHN, Rathore V, Rawat AK, Tamrakar AK, Srivastava AK, Trivedi P.  (2013)  Design, synthesis and biological evaluation of novel arylidine-malononitrile derivatives as non-carboxylic inhibitors of protein tyrosine phosphatase 1B,  22  (11): [10.1007/s00044-013-0528-1]

Source

Source(1):

• Scientific Literature