N-(3-(5-((4-chlorobenzyl)sulfanyl)-1,3,4-oxadiazol-2-yl)-5-nitrophenyl)acetamide

ID: ALA4103580

PubChem CID: 137657866

Max Phase: Preclinical

Molecular Formula: C17H13ClN4O4S

Molecular Weight: 404.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc(-c2nnc(SCc3ccc(Cl)cc3)o2)cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C17H13ClN4O4S/c1-10(23)19-14-6-12(7-15(8-14)22(24)25)16-20-21-17(26-16)27-9-11-2-4-13(18)5-3-11/h2-8H,9H2,1H3,(H,19,23)

Standard InChI Key:  CMDUEJAUPPVOGE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   15.4455  -18.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0623  -18.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8349  -18.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9906  -17.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3738  -17.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6012  -17.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7785  -17.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4493  -17.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1005  -17.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8342  -16.6757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0186  -16.6757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8823  -17.6859    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.4790  -17.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2609  -17.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4460  -18.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2280  -18.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8247  -17.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6395  -17.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8576  -16.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6065  -18.0781    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.9066  -19.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5234  -20.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3677  -20.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2960  -19.8991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9809  -16.9513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2083  -17.2176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1366  -16.1491    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
 17 20  1  0
  2 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 25 26  2  0
 25 27  1  0
  6 25  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4103580

   ---

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: 404.84

Molecular Weight (Monoisotopic): 404.0346

AlogP: 4.55

#Rotatable Bonds: 6

Polar Surface Area: 111.16

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.21

CX Basic pKa: ┄

CX LogP: 3.69

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.36

Np Likeness Score: -2.40

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