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

ID: ALA4104413

PubChem CID: 137656951

Max Phase: Preclinical

Molecular Formula: C15H8Cl2N4O5S

Molecular Weight: 427.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(-c2nnc(SCc3ccc(Cl)cc3Cl)o2)cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C15H8Cl2N4O5S/c16-10-2-1-8(13(17)5-10)7-27-15-19-18-14(26-15)9-3-11(20(22)23)6-12(4-9)21(24)25/h1-6H,7H2

Standard InChI Key:  SRVNEAMSJUDEJT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    3.5343   -4.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1511   -5.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9237   -4.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0794   -4.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626   -3.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6900   -3.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8673   -3.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5381   -4.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1893   -3.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9230   -3.0982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1074   -3.0982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9711   -4.1084    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5678   -3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3497   -3.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5349   -4.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3168   -4.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9135   -4.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7284   -3.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9464   -3.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7613   -2.4334    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.6953   -4.5006    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0693   -3.3727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2967   -3.6390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -2.5705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9945   -6.0530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6114   -6.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219   -6.3192    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
 17 21  1  0
 22 23  2  0
 22 24  1  0
  6 22  1  0
 25 26  2  0
 25 27  1  0
  2 25  1  0
M  CHG  4  22   1  24  -1  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4104413

   ---

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: 427.23

Molecular Weight (Monoisotopic): 425.9592

AlogP: 5.15

#Rotatable Bonds: 6

Polar Surface Area: 125.20

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.00

CX LogD: 5.00

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.30

Np Likeness Score: -2.01

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