2-[(2-Chlorobenzyl)sulfanyl]-5-(3,5-dinitrophenyl)-1,3,4-oxadiazole

ID: ALA4102014

PubChem CID: 137661943

Max Phase: Preclinical

Molecular Formula: C15H9ClN4O5S

Molecular Weight: 392.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(-c2nnc(SCc3ccccc3Cl)o2)cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C15H9ClN4O5S/c16-13-4-2-1-3-9(13)8-26-15-18-17-14(25-15)10-5-11(19(21)22)7-12(6-10)20(23)24/h1-7H,8H2

Standard InChI Key:  FYGBVKUZYWSJKU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   31.4017   -3.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0186   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7912   -3.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9469   -2.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3301   -2.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5575   -2.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7347   -2.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4056   -3.0067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0567   -2.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7905   -1.7403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9748   -1.7403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8386   -2.7505    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.4353   -2.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2172   -2.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4023   -3.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1842   -3.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7810   -2.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5957   -2.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8139   -1.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6288   -1.0756    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.9363   -2.0150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1637   -2.2812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0921   -1.2128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8624   -4.6955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4793   -5.2315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0898   -4.9617    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
 19 20  1  0
 21 22  2  0
 21 23  1  0
  6 21  1  0
 24 25  2  0
 24 26  1  0
  2 24  1  0
M  CHG  4  21   1  23  -1  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4102014

   ---

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: 392.78

Molecular Weight (Monoisotopic): 391.9982

AlogP: 4.50

#Rotatable Bonds: 6

Polar Surface Area: 125.20

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.40

CX LogD: 4.40

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.34

Np Likeness Score: -2.04

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