2-Cyclohexylsulfanyl-5-(3,5-dinitrophenyl)-1,3,4-oxadiazole

ID: ALA4099328

PubChem CID: 137661640

Max Phase: Preclinical

Molecular Formula: C14H14N4O5S

Molecular Weight: 350.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(-c2nnc(SC3CCCCC3)o2)cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C14H14N4O5S/c19-17(20)10-6-9(7-11(8-10)18(21)22)13-15-16-14(23-13)24-12-4-2-1-3-5-12/h6-8,12H,1-5H2

Standard InChI Key:  DCTZQVHWNKWSBK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   16.3982  -10.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0150  -11.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7876  -10.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9434  -10.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3265   -9.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5539   -9.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7312   -9.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4020  -10.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0532   -9.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7869   -8.9778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9713   -8.9778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8350   -9.9879    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.4318   -9.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2136   -9.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8103   -9.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6252   -8.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8433   -8.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2465   -8.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9345   -9.2538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1619   -9.5201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0903   -8.4516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8596  -11.9370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4765  -12.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0870  -12.2032    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  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 13  1  0
 19 20  2  0
 19 21  1  0
  6 19  1  0
 22 23  2  0
 22 24  1  0
  2 22  1  0
M  CHG  4  19   1  21  -1  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4099328

   ---

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: 350.36

Molecular Weight (Monoisotopic): 350.0685

AlogP: 3.98

#Rotatable Bonds: 5

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: 3.76

CX LogD: 3.76

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.59

Np Likeness Score: -1.48

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