5-((4-Chlorobenzyl)thio)-1,3-dimethyl-6-((E)-((E)-3-phenylallylidene)amino)-3,3a,6,6a-tetrahydroimidazo[4,5-d]imidazol-2(1H)-one

ID: ALA4209405

PubChem CID: 145964036

Max Phase: Preclinical

Molecular Formula: C22H22ClN5OS

Molecular Weight: 439.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)N(C)C2C1N=C(SCc1ccc(Cl)cc1)N2/N=C/C=C/c1ccccc1

Standard InChI:  InChI=1S/C22H22ClN5OS/c1-26-19-20(27(2)22(26)29)28(24-14-6-9-16-7-4-3-5-8-16)21(25-19)30-15-17-10-12-18(23)13-11-17/h3-14,19-20H,15H2,1-2H3/b9-6+,24-14+

Standard InChI Key:  WOXBZPMTFJECAI-XWJCGCQVSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   21.2187  -21.0883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2190  -19.7648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7411  -20.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9984  -20.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9960  -20.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7726  -21.0911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2549  -20.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7764  -19.7687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9239  -20.4266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0721  -20.4335    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.0311  -18.9922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8309  -18.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0857  -18.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8855  -17.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9657  -18.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4827  -19.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1403  -17.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9647  -21.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2999  -19.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9412  -16.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1960  -16.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6507  -15.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8473  -15.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5962  -16.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7041  -20.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5205  -20.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9319  -19.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5210  -19.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7059  -19.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7491  -19.7363    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
  4  2  1  0
  2  3  1  0
  3  1  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  4  1  0
  3  9  2  0
  7 10  1  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 10 16  1  0
 14 17  1  0
  1 18  1  0
 16 19  1  0
 17 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 17  1  0
 19 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 19  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4209405

   ---

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: 439.97

Molecular Weight (Monoisotopic): 439.1234

AlogP: 4.59

#Rotatable Bonds: 5

Polar Surface Area: 51.51

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.57

CX Basic pKa: 2.43

CX LogP: 5.13

CX LogD: 5.13

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.64

Np Likeness Score: -0.83

References

1. Gazieva GA, Anikina LV, Nechaeva TV, Pukhov SA, Karpova TB, Popkov SV, Nelyubina YV, Kolotyrkina NG, Kravchenko AN..  (2017)  Synthesis and biological evaluation of new substituted thioglycolurils, their analogues and derivatives.,  140  [PMID:28923382] [10.1016/j.ejmech.2017.09.009]

Source

Source(1):

• Scientific Literature