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

ID: ALA2296210

PubChem CID: 76320366

Max Phase: Preclinical

Molecular Formula: C20H13FN4O2S

Molecular Weight: 392.42

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H13FN4O2S/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:  SXRIVDRWVHHQAN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   17.5967  -15.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0036  -14.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5962  -13.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7777  -13.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3744  -14.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8208  -14.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3002  -15.2646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0784  -15.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0773  -14.1938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2984  -13.9433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7941  -15.4063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.4936  -14.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4776  -14.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1771  -13.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8927  -14.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9034  -14.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6182  -15.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3187  -14.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2999  -14.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5846  -13.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0348  -15.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7338  -14.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4499  -15.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7166  -14.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7028  -13.2666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1627  -15.6836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5573  -14.6102    0.0000 F   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:

   

   ALA2296210

   2-[[4-[2-[[5-(4-Fluorophenyl)-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: 392.42

Molecular Weight (Monoisotopic): 392.0743

AlogP: 4.48

#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: 4.02

CX LogD: 4.02

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.33

Np Likeness Score: -1.97

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