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

ID: ALA2296211

PubChem CID: 76323998

Max Phase: Preclinical

Molecular Formula: C21H16N4O2S

Molecular Weight: 388.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2nnc(SCCOc3ccc(C=C(C#N)C#N)cc3)o2)cc1

Standard InChI:  InChI=1S/C21H16N4O2S/c1-15-2-6-18(7-3-15)20-24-25-21(27-20)28-11-10-26-19-8-4-16(5-9-19)12-17(13-22)14-23/h2-9,12H,10-11H2,1H3

Standard InChI Key:  XEMVHRGBDDHGGX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.2876  -19.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802  -19.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0617  -19.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585  -19.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1048  -19.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5842  -20.6506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3624  -20.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3613  -19.5798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5824  -19.3293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0781  -20.7923    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7776  -20.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7616  -19.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4611  -19.1304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1767  -19.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1874  -20.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9022  -20.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6027  -20.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5839  -19.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8687  -19.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3188  -20.7056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0178  -20.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7339  -20.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0007  -19.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9868  -18.6526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4467  -21.0696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8413  -19.9962    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
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  3  7  1  0
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  9 10  2  0
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  9 12  1  0
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 17 18  1  0
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 23 25  1  0
 25 26  3  0
 24 27  3  0
  6 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296211

   2-[[4-[2-[[5-(4-Methylphenyl)-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: 388.45

Molecular Weight (Monoisotopic): 388.0994

AlogP: 4.65

#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: 4.39

CX LogD: 4.39

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.33

Np Likeness Score: -1.79

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