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

ID: ALA4101143

PubChem CID: 137660526

Max Phase: Preclinical

Molecular Formula: C15H11ClN4O3S

Molecular Weight: 362.80

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H11ClN4O3S/c16-11-3-1-9(2-4-11)8-24-15-19-18-14(23-15)10-5-12(17)7-13(6-10)20(21)22/h1-7H,8,17H2

Standard InChI Key:  INDMVRPYSWGEPM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.5850   -4.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2018   -4.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745   -4.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1302   -3.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134   -3.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7408   -3.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9180   -3.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5888   -3.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2400   -3.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9738   -2.6081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1582   -2.6081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0218   -3.6184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6185   -3.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4005   -3.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5856   -4.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3675   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9642   -3.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7791   -2.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9972   -2.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7461   -4.0105    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0461   -5.5617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -2.8858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3485   -3.1521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -2.0836    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
 22 23  2  0
 22 24  1  0
  6 22  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4101143

   ---

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: 362.80

Molecular Weight (Monoisotopic): 362.0240

AlogP: 4.17

#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: 3.63

CX LogD: 3.63

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.31

Np Likeness Score: -2.16

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