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

ID: ALA2296206

PubChem CID: 76323997

Max Phase: Preclinical

Molecular Formula: C21H16N4O3S

Molecular Weight: 404.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1-c1nnc(SCCOc2ccc(C=C(C#N)C#N)cc2)o1

Standard InChI:  InChI=1S/C21H16N4O3S/c1-26-19-5-3-2-4-18(19)20-24-25-21(28-20)29-11-10-27-17-8-6-15(7-9-17)12-16(13-22)14-23/h2-9,12H,10-11H2,1H3

Standard InChI Key:  OSAZHQQWPVYINV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   19.3260   -4.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7329   -3.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3255   -2.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5070   -2.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1038   -3.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5501   -3.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0295   -4.1871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8077   -3.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8066   -3.1163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0277   -2.8658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5234   -4.3288    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.2229   -3.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2069   -3.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9064   -2.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6220   -3.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6327   -3.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3475   -4.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0480   -3.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0292   -3.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3140   -2.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7641   -4.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4631   -3.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1792   -4.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4460   -3.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4321   -2.1891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8920   -4.6061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7330   -2.1140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5502   -2.1128    0.0000 C   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
  4 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296206

   2-[[4-[2-[[5-(2-Methoxyphenyl)-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: 404.45

Molecular Weight (Monoisotopic): 404.0943

AlogP: 4.35

#Rotatable Bonds: 8

Polar Surface Area: 104.96

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.31

Np Likeness Score: -1.63

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