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

ID: ALA2296212

PubChem CID: 76316651

Max Phase: Preclinical

Molecular Formula: C20H13N5O4S

Molecular Weight: 419.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CC(C#N)=Cc1ccc(OCCSc2nnc(-c3cccc([N+](=O)[O-])c3)o2)cc1

Standard InChI:  InChI=1S/C20H13N5O4S/c21-12-15(13-22)10-14-4-6-18(7-5-14)28-8-9-30-20-24-23-19(29-20)16-2-1-3-17(11-16)25(26)27/h1-7,10-11H,8-9H2

Standard InChI Key:  QWZZRIQXEKNFMS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.9126  -25.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7280  -25.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1349  -24.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7275  -24.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9090  -24.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057  -24.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9521  -24.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4315  -25.6322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2097  -25.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2086  -24.5614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4297  -24.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9254  -25.7739    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6249  -25.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6089  -24.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3084  -24.1120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0240  -24.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0347  -25.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4500  -25.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4312  -24.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7159  -24.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1661  -25.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8651  -25.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5812  -25.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8479  -24.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8341  -23.6342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2940  -26.0512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4955  -23.5622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6784  -23.5653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9015  -22.8530    0.0000 O   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
 28 29  2  0
 28 30  1  0
  5 28  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2296212

   2-[[4-[2-[[5-(3-Nitrophenyl)-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: 419.42

Molecular Weight (Monoisotopic): 419.0688

AlogP: 4.25

#Rotatable Bonds: 8

Polar Surface Area: 138.87

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.82

CX LogD: 3.82

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.17

Np Likeness Score: -2.01

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