(5Z)-5-(3,4-Dimethoxybenzylidene)-3-phenyl-2-thioxoimidazolidin-4-one

ID: ALA4204445

PubChem CID: 1722365

Max Phase: Preclinical

Molecular Formula: C18H16N2O3S

Molecular Weight: 340.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2\NC(=S)N(c3ccccc3)C2=O)cc1OC

Standard InChI:  InChI=1S/C18H16N2O3S/c1-22-15-9-8-12(11-16(15)23-2)10-14-17(21)20(18(24)19-14)13-6-4-3-5-7-13/h3-11H,1-2H3,(H,19,24)/b14-10-

Standard InChI Key:  YCHBBPYKSIETDT-UVTDQMKNSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   14.4411  -14.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2583  -14.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5127  -13.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8497  -12.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1910  -13.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8485  -12.1299    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.7379  -14.8676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2865  -13.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8929  -13.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6699  -13.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8415  -12.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2301  -12.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4555  -12.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9599  -14.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1473  -14.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8201  -14.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0083  -13.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5262  -14.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8618  -15.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6726  -15.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6772  -13.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1588  -12.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7135  -14.5192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3811  -13.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  4  6  2  0
  2  7  2  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  3  8  1  0
  1 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 17 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4204445

   5-(3,4-Dimethoxybenzylidene)-3-phenyl-2-thioxo-4-imidazolidinone

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: 340.40

Molecular Weight (Monoisotopic): 340.0882

AlogP: 2.97

#Rotatable Bonds: 4

Polar Surface Area: 50.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.73

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: 3.13

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.68

Np Likeness Score: -0.98

References

1. Maccari R, Ettari R, Adornato I, Naß A, Wolber G, Bitto A, Mannino F, Aliquò F, Bruno G, Nicolò F, Previti S, Grasso S, Zappalà M, Ottanà R..  (2018)  Identification of 2-thioxoimidazolidin-4-one derivatives as novel noncovalent proteasome and immunoproteasome inhibitors.,  28  (3): [PMID:29292224] [10.1016/j.bmcl.2017.12.053]

Source

Source(1):

• Scientific Literature