3-(5-(Benzylsulfanyl)-1,3,4-oxadiazol-2-yl)-5-nitroaniline

ID: ALA4093390

PubChem CID: 137653503

Max Phase: Preclinical

Molecular Formula: C15H12N4O3S

Molecular Weight: 328.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H12N4O3S/c16-12-6-11(7-13(8-12)19(20)21)14-17-18-15(22-14)23-9-10-4-2-1-3-5-10/h1-8H,9,16H2

Standard InChI Key:  IYJQSAVPLVSKIJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   30.1016   -9.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7185  -10.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4911  -10.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6468   -9.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0300   -8.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2574   -9.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4346   -9.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1055   -9.6485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7565   -9.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4904   -8.3821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6747   -8.3821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5385   -9.3924    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.1352   -8.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9171   -9.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1022   -9.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8841  -10.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4809   -9.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2956   -8.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5138   -8.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5628  -11.3357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6374   -8.6600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8647   -8.9262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7931   -7.8578    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
 21 22  2  0
 21 23  1  0
  6 21  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4093390

   ---

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: 328.35

Molecular Weight (Monoisotopic): 328.0630

AlogP: 3.52

#Rotatable Bonds: 5

Polar Surface Area: 108.08

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.53

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.33

Np Likeness Score: -2.02

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