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

ID: ALA208987

PubChem CID: 24205067

Max Phase: Preclinical

Molecular Formula: C15H16N6O3S5

Molecular Weight: 488.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)NC2=NCCN2C(=S)SN2CCn3c2nsc3=S)cc1

Standard InChI:  InChI=1S/C15H16N6O3S5/c1-24-10-2-4-11(5-3-10)29(22,23)18-12-16-6-7-19(12)15(26)28-21-9-8-20-13(21)17-27-14(20)25/h2-5H,6-9H2,1H3,(H,16,18)

Standard InChI Key:  WAGGPKJMAYNWJX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    1.4130   -5.4660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1856   -5.7630    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049   -5.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -4.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -4.4288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986   -3.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5259   -3.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0066   -3.9516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5300   -5.1636    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1855   -3.9062    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298   -3.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0527   -3.1928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1855   -2.4794    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391   -2.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3243   -2.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3243   -3.6043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391   -3.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2840   -4.6444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8706   -5.2310    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2840   -5.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4533   -4.6444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4533   -5.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2460   -5.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8284   -6.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6153   -6.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8146   -7.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2355   -6.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1963   -7.5603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9823   -8.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  0
  8  4  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA208987

   2-(4-Methoxy-benzenesulfonylimino)-imidazolidine-1-carbodith ioic 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: 488.67

Molecular Weight (Monoisotopic): 487.9887

AlogP: 2.09

#Rotatable Bonds: 4

Polar Surface Area: 92.06

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.03

CX Basic pKa: 1.68

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -1.46

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