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

ID: ALA4095835

PubChem CID: 137653153

Max Phase: Preclinical

Molecular Formula: C16H9ClF3N3O3S

Molecular Weight: 415.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(-c2nnc(SCc3ccc(Cl)cc3)o2)cc(C(F)(F)F)c1

Standard InChI:  InChI=1S/C16H9ClF3N3O3S/c17-12-3-1-9(2-4-12)8-27-15-22-21-14(26-15)10-5-11(16(18,19)20)7-13(6-10)23(24)25/h1-7H,8H2

Standard InChI Key:  WKEPDXWOQWKSFD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    3.4765  -12.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0933  -12.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8659  -12.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0217  -11.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4049  -11.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6322  -11.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095  -11.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4803  -11.7926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1315  -11.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8652  -10.5262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0496  -10.5262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9133  -11.5364    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5100  -10.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2920  -11.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4771  -12.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2590  -12.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8557  -11.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6706  -10.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8887  -10.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6375  -11.9286    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0119  -10.8018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393  -11.0680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -9.9996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376  -13.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1650  -13.7460    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5544  -14.0158    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7228  -14.2678    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
 17 20  1  0
 21 22  2  0
 21 23  1  0
  6 21  1  0
  2 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4095835

   ---

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: 415.78

Molecular Weight (Monoisotopic): 415.0005

AlogP: 5.61

#Rotatable Bonds: 5

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.33

CX LogD: 5.33

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.31

Np Likeness Score: -2.24

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