2-[(E)-4-trifluoromethoxy-benzenesulfonylimino]-imidazolidine-1-carbodithioic acid 3-thioxo-5,6-dihydro-imidazo[2,1-c][1,2,4]thiadiazol-7-yl ester

ID: ALA207439

PubChem CID: 24205510

Max Phase: Preclinical

Molecular Formula: C15H13F3N6O3S5

Molecular Weight: 542.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(NC1=NCCN1C(=S)SN1CCn2c1nsc2=S)c1ccc(OC(F)(F)F)cc1

Standard InChI:  InChI=1S/C15H13F3N6O3S5/c16-15(17,18)27-9-1-3-10(4-2-9)32(25,26)21-11-19-5-6-22(11)14(29)31-24-8-7-23-12(24)20-30-13(23)28/h1-4H,5-8H2,(H,19,21)

Standard InChI Key:  WXZKRRQPTAOTBE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   11.6803  -11.9220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4530  -12.2190    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.9723  -11.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7257  -11.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5244  -10.8847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5660  -10.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7932   -9.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2738  -10.4074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7976  -11.6195    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4525  -10.3620    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0372   -9.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2143   -9.6486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4525   -8.9350    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7278   -8.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9424   -9.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9424  -10.0599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7278  -10.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9828  -11.1004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3962  -11.6870    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9828  -12.2698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8134  -11.1004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8134  -12.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0207  -12.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4381  -12.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513  -13.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4522  -13.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0312  -13.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0702  -14.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2842  -14.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4902  -15.6005    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0796  -14.6003    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4907  -15.0291    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  2  0
 19 22  1  0
 22 23  2  0
  1  2  1  0
 23 24  1  0
  2  3  1  0
 24 25  2  0
  3  5  1  0
 25 26  1  0
  4  1  2  0
 26 27  2  0
 27 22  1  0
  4  5  1  0
 25 28  1  0
  5  6  1  0
 28 29  1  0
  6  7  1  0
 29 30  1  0
  7  8  1  0
 29 31  1  0
  8  4  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA207439

   2-(4-Trifluoromethoxy-benzenesulfonylimino)-imidazolidine-1-carbodithioic acid 3-thioxo-5,1-c][1,2,4]thiadiazol-7-yl ester

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: 542.64

Molecular Weight (Monoisotopic): 541.9605

AlogP: 2.98

#Rotatable Bonds: 4

Polar Surface Area: 92.06

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.87

CX Basic pKa: 1.47

CX LogP: 5.20

CX LogD: 5.19

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -1.58

References

1. Saczewski J, Brzozowski Z, Saczewski F, Bednarski PJ, Liebeke M, Gdaniec M..  (2006)  Synthesis and in vitro anti-tumor activity of N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides.,  16  (14): [PMID:16682194] [10.1016/j.bmcl.2006.04.067]

Source

Source(1):

• Scientific Literature