2-(Benzylsulfanyl)-5-(3-nitro-5-(trifluoromethyl)phenyl)-1,3,4-oxadiazole

ID: ALA4103592

PubChem CID: 137658256

Max Phase: Preclinical

Molecular Formula: C16H10F3N3O3S

Molecular Weight: 381.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(-c2nnc(SCc3ccccc3)o2)cc(C(F)(F)F)c1

Standard InChI:  InChI=1S/C16H10F3N3O3S/c17-16(18,19)12-6-11(7-13(8-12)22(23)24)14-20-21-15(25-14)26-9-10-4-2-1-3-5-10/h1-8H,9H2

Standard InChI Key:  AIXMLNIHIQKGEF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   26.8494  -17.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4663  -18.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2389  -17.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3946  -17.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7778  -16.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0052  -16.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1824  -16.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8533  -17.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5043  -16.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2382  -16.0980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4225  -16.0980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2863  -17.1081    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.8830  -16.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6649  -16.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8500  -17.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6319  -17.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2286  -17.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0434  -16.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2616  -16.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3844  -16.3737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6118  -16.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5402  -15.5715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3105  -19.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5379  -19.3178    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.9274  -19.5875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.0953  -19.8396    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
  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
 20 21  2  0
 20 22  1  0
  6 20  1  0
  2 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4103592

   ---

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: 381.33

Molecular Weight (Monoisotopic): 381.0395

AlogP: 4.96

#Rotatable Bonds: 5

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.73

CX LogD: 4.73

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.35

Np Likeness Score: -2.13

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