1-Methyl-5-(methylthio)-6-((E)-((E)-3-(2-nitrophenyl)allylidene)amino)-3-phenyl-3,3a,6,6a-tetrahydroimidazo[4,5-d]imidazol-2(1H)-one

ID: ALA4217246

PubChem CID: 145973766

Max Phase: Preclinical

Molecular Formula: C21H20N6O3S

Molecular Weight: 436.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSC1=NC2C(N(C)C(=O)N2c2ccccc2)N1/N=C/C=C/c1ccccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C21H20N6O3S/c1-24-19-18(25(21(24)28)16-11-4-3-5-12-16)23-20(31-2)26(19)22-14-8-10-15-9-6-7-13-17(15)27(29)30/h3-14,18-19H,1-2H3/b10-8+,22-14+

Standard InChI Key:  QHADGTJMAAEEKC-ONRJMHNSSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   34.7395   -5.1737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7398   -3.8502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2619   -4.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5192   -4.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5168   -4.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2934   -5.1765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7757   -4.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2972   -3.8541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.4447   -4.5120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5929   -4.5189    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.5519   -3.0776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3517   -2.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6065   -2.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4063   -1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4865   -3.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4855   -5.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0035   -3.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6611   -1.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4620   -1.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7168   -0.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1715    0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3681    0.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1170   -0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6868   -6.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4327   -6.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9787   -7.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7819   -7.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0322   -6.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0060   -1.6378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.8063   -1.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.7491   -2.4136    0.0000 O   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
  1 16  1  0
 10 17  1  0
 14 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 16 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 16  1  0
 29 30  2  0
 29 31  1  0
 19 29  1  0
M  CHG  2  29   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4217246

   ---

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: 436.50

Molecular Weight (Monoisotopic): 436.1318

AlogP: 3.85

#Rotatable Bonds: 5

Polar Surface Area: 94.65

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.42

CX Basic pKa: 2.23

CX LogP: 4.50

CX LogD: 4.50

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -1.03

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