5-(3,5-Dinitrophenyl)-2-[(4-nitrobenzyl)sulfanyl]-1,3,4-oxadiazole

ID: ALA4094283

PubChem CID: 137653300

Max Phase: Preclinical

Molecular Formula: C15H9N5O7S

Molecular Weight: 403.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(CSc2nnc(-c3cc([N+](=O)[O-])cc([N+](=O)[O-])c3)o2)cc1

Standard InChI:  InChI=1S/C15H9N5O7S/c21-18(22)11-3-1-9(2-4-11)8-28-15-17-16-14(27-15)10-5-12(19(23)24)7-13(6-10)20(25)26/h1-7H,8H2

Standard InChI Key:  GMPAHBBUVIFYBC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   16.6784   -4.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2952   -5.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0678   -4.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2236   -4.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6067   -3.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8341   -3.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0114   -3.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6823   -4.2772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3333   -3.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0671   -3.0108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2515   -3.0108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1152   -4.0211    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.7120   -3.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4938   -3.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6789   -4.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4609   -4.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0576   -4.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8724   -3.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0906   -3.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2149   -3.2857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4422   -3.5519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3706   -2.4835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1416   -5.9671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7584   -6.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3690   -6.2332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8418   -4.4129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4385   -3.8546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0269   -5.2088    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
 20 21  2  0
 20 22  1  0
  6 20  1  0
 23 24  2  0
 23 25  1  0
  2 23  1  0
 26 27  2  0
 26 28  1  0
 17 26  1  0
M  CHG  6  20   1  22  -1  23   1  25  -1  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4094283

   ---

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: 403.33

Molecular Weight (Monoisotopic): 403.0223

AlogP: 3.75

#Rotatable Bonds: 7

Polar Surface Area: 168.34

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.73

CX LogD: 3.73

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: -1.67

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