5-[5-(Azidomethyl)-1,3,4-oxadiazol-2-yl]-2-benzylthio-4-chlorobenzenesulfonamide

ID: ALA4097363

PubChem CID: 137658709

Max Phase: Preclinical

Molecular Formula: C16H13ClN6O3S2

Molecular Weight: 436.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=NCc1nnc(-c2cc(S(N)(=O)=O)c(SCc3ccccc3)cc2Cl)o1

Standard InChI:  InChI=1S/C16H13ClN6O3S2/c17-12-7-13(27-9-10-4-2-1-3-5-10)14(28(19,24)25)6-11(12)16-22-21-15(26-16)8-20-23-18/h1-7H,8-9H2,(H2,19,24,25)

Standard InChI Key:  FOTBPGKLEHRJPM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    8.9602   -6.0134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5557   -5.3076    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1468   -6.0108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4329   -4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4318   -4.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1398   -5.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8495   -4.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8467   -4.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1380   -3.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7251   -3.6734    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5528   -3.6669    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5497   -2.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2559   -2.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9604   -2.8479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6661   -2.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6635   -1.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9492   -1.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2465   -1.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7265   -5.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9802   -4.9797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4329   -5.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8409   -6.2946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6404   -6.1252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -5.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2884   -4.7537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2649   -4.8986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4758   -4.6676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344   -4.5753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  4 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  2  0
  5 19  1  0
 21 24  1  0
 24 25  1  0
  7  2  1  0
  2 26  1  0
 25 27  2  0
 27 28  2  0
M  CHG  2  27   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4097363

   ---

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: 436.91

Molecular Weight (Monoisotopic): 436.0179

AlogP: 4.14

#Rotatable Bonds: 7

Polar Surface Area: 147.84

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.11

CX Basic pKa: ┄

CX LogP: 2.56

CX LogD: 2.44

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.25

Np Likeness Score: -1.63

References

1. Sławiński J, Szafrański K, Pogorzelska A, Żołnowska B, Kawiak A, Macur K, Belka M, Bączek T..  (2017)  Novel 2-benzylthio-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides with anticancer activity: Synthesis, QSAR study, and metabolic stability.,  132  [PMID:28364658] [10.1016/j.ejmech.2017.03.039]

Source

Source(1):

• Scientific Literature