2-((3,5-Dinitrobenzyl)sulfanyl)-5-(3-(piperidin-1-yl)propyl)-1,3,4-oxadiazole

ID: ALA4097119

PubChem CID: 137659663

Max Phase: Preclinical

Molecular Formula: C17H21N5O5S

Molecular Weight: 407.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(CSc2nnc(CCCN3CCCCC3)o2)cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C17H21N5O5S/c23-21(24)14-9-13(10-15(11-14)22(25)26)12-28-17-19-18-16(27-17)5-4-8-20-6-2-1-3-7-20/h9-11H,1-8,12H2

Standard InChI Key:  JCYQVPHKBHCOCJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   11.2933  -15.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8788  -16.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2836  -16.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1029  -16.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5156  -16.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1084  -15.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0616  -16.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6486  -16.7323    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8314  -16.7272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3545  -16.0644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5757  -16.3121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5707  -17.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3463  -17.3865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9067  -17.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1622  -17.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4981  -17.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5203  -14.6157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1134  -13.9070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3375  -14.6176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5111  -17.4573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3283  -17.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0998  -18.1634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7536  -17.4080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6743  -16.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9339  -16.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671  -16.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457  -17.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0911  -17.8891    0.0000 C   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
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 17 18  2  0
 17 19  1  0
  6 17  1  0
 20 21  2  0
 20 22  1  0
  4 20  1  0
 16 23  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  CHG  4  17   1  19  -1  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4097119

   ---

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: 407.45

Molecular Weight (Monoisotopic): 407.1263

AlogP: 3.60

#Rotatable Bonds: 9

Polar Surface Area: 128.44

Molecular Species: BASE

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.67

CX LogP: 3.16

CX LogD: 1.87

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.35

Np Likeness Score: -2.09

References

1. Roh J, Karabanovich G, Vlčková H, Carazo A, Němeček J, Sychra P, Valášková L, Pavliš O, Stolaříková J, Klimešová V, Vávrová K, Pávek P, Hrabálek A..  (2017)  Development of water-soluble 3,5-dinitrophenyl tetrazole and oxadiazole antitubercular agents.,  25  (20): [PMID:28835350] [10.1016/j.bmc.2017.08.010]

Source

Source(1):

• Scientific Literature