N-(3-nitro-5-(5-((4-nitrobenzyl)sulfanyl)-1,3,4-oxadiazol-2-yl)phenyl)acetamide

ID: ALA4100179

PubChem CID: 137660043

Max Phase: Preclinical

Molecular Formula: C17H13N5O6S

Molecular Weight: 415.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc(-c2nnc(SCc3ccc([N+](=O)[O-])cc3)o2)cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C17H13N5O6S/c1-10(23)18-13-6-12(7-15(8-13)22(26)27)16-19-20-17(28-16)29-9-11-2-4-14(5-3-11)21(24)25/h2-8H,9H2,1H3,(H,18,23)

Standard InChI Key:  FSKSBZVKEVDYFK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   26.8768  -10.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4936  -10.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2662  -10.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4220   -9.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8051   -9.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0325   -9.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2098   -9.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8806  -10.0550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5317   -9.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2655   -8.7886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4499   -8.7886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3136   -9.7988    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.9104   -9.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6922   -9.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8773  -10.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6592  -10.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2559   -9.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0708   -9.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2890   -8.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3378  -11.7421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9548  -12.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7989  -13.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7274  -12.0120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4133   -9.0638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6407   -9.3300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5691   -8.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0399  -10.1902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6366   -9.6319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2250  -10.9862    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
  4  7  1  0
  7  8  1  0
  8  9  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  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 24 25  2  0
 24 26  1  0
  6 24  1  0
 27 28  2  0
 27 29  1  0
 17 27  1  0
M  CHG  4  24   1  26  -1  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4100179

   ---

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: 415.39

Molecular Weight (Monoisotopic): 415.0587

AlogP: 3.80

#Rotatable Bonds: 7

Polar Surface Area: 154.30

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.21

CX Basic pKa: ┄

CX LogP: 3.03

CX LogD: 3.03

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: -2.09

References

1. Karabanovich G, Němeček J, Valášková L, Carazo A, Konečná K, Stolaříková J, Hrabálek A, Pavliš O, Pávek P, Vávrová K, Roh J, Klimešová V..  (2017)  S-substituted 3,5-dinitrophenyl 1,3,4-oxadiazole-2-thiols and tetrazole-5-thiols as highly efficient antitubercular agents.,  126  [PMID:27907875] [10.1016/j.ejmech.2016.11.041]

Source

Source(1):

• Scientific Literature