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

ID: ALA4095824

PubChem CID: 137652686

Max Phase: Preclinical

Molecular Formula: C17H14N4O4S

Molecular Weight: 370.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc(-c2nnc(SCc3ccccc3)o2)cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C17H14N4O4S/c1-11(22)18-14-7-13(8-15(9-14)21(23)24)16-19-20-17(25-16)26-10-12-5-3-2-4-6-12/h2-9H,10H2,1H3,(H,18,22)

Standard InChI Key:  ZGVIOUKDVNMGPM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   16.2465   -3.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8634   -4.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6360   -3.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7917   -3.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1749   -2.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4023   -2.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5795   -2.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2504   -3.2822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9015   -2.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6353   -2.0158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8196   -2.0158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6834   -3.0260    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.2801   -2.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0620   -2.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2471   -3.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0290   -3.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6258   -3.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4405   -2.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6587   -2.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7077   -4.9693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3245   -5.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1688   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0971   -5.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7816   -2.2916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0089   -2.5578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9373   -1.4894    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
  2 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 24 25  2  0
 24 26  1  0
  6 24  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4095824

   ---

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: 370.39

Molecular Weight (Monoisotopic): 370.0736

AlogP: 3.90

#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: 3.09

CX LogD: 3.09

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.40

Np Likeness Score: -2.28

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