2-(4-nitrophenoxy)-N-(5-phenyl-1,3,4-oxadiazol-2-ylcarbamothioyl)acetamide

ID: ALA2288970

PubChem CID: 14690720

Max Phase: Preclinical

Molecular Formula: C17H13N5O5S

Molecular Weight: 399.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(COc1ccc([N+](=O)[O-])cc1)NC(=S)Nc1nnc(-c2ccccc2)o1

Standard InChI:  InChI=1S/C17H13N5O5S/c23-14(10-26-13-8-6-12(7-9-13)22(24)25)18-17(28)19-16-21-20-15(27-16)11-4-2-1-3-5-11/h1-9H,10H2,(H2,18,19,21,23,28)

Standard InChI Key:  HJMRKZFEJHKPRU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   12.8109   -8.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0953   -7.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3857   -8.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3906   -8.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1108   -9.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174   -8.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5363   -9.3162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5438  -10.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2627  -10.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2702  -11.3742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9741  -10.1290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6930  -10.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4044  -10.1159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7005  -11.3612    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.1233  -10.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2207  -11.3399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0301  -11.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4364  -10.7853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8783  -10.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3724  -12.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8913  -12.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2333  -13.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0562  -13.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5358  -13.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1911  -12.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6641   -7.6888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -8.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6592   -6.8630    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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  2  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 17 20  1  0
 26 27  2  0
 26 28  1  0
  3 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288970

   2-(4-nitrophenoxy)-N-[(5-phenyl-1,3,4-oxadiazol-2-yl)carbamothioyl]acetamide

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: 399.39

Molecular Weight (Monoisotopic): 399.0637

AlogP: 2.54

#Rotatable Bonds: 6

Polar Surface Area: 132.42

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.97

CX Basic pKa: ┄

CX LogP: 2.90

CX LogD: 2.89

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: -2.21

References

1. MISHRA B, NIZAMUDDIN.  (1990)  Synthesis and Fungicidal Activities of Some 1-Aryloxyaceto-3-(5-aryl-1, 3, 4-oxadiazol-2-yl) thioureas and Corresponding Oxadiazolo [3, 2-a]-s-triazines,  15  (3): [10.1584/jpestics.15.353]

Source

Source(1):

• Scientific Literature