(5Z)-5-(3-Phenoxybenzylidene)-3-phenyl-2-thioxoimidazolidin-4-one

ID: ALA4217578

PubChem CID: 8108561

Max Phase: Preclinical

Molecular Formula: C22H16N2O2S

Molecular Weight: 372.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2cccc(Oc3ccccc3)c2)NC(=S)N1c1ccccc1

Standard InChI:  InChI=1S/C22H16N2O2S/c25-21-20(23-22(27)24(21)17-9-3-1-4-10-17)15-16-8-7-13-19(14-16)26-18-11-5-2-6-12-18/h1-15H,(H,23,27)/b20-15-

Standard InChI Key:  XIOSASYQUPWKOP-HKWRFOASSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   25.1265   -3.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9437   -3.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1981   -2.3807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5351   -1.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8764   -2.3807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5339   -1.0813    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.4233   -3.8190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9719   -2.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5783   -2.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3553   -2.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5269   -1.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9155   -1.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1409   -1.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6453   -3.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8327   -3.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5055   -2.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6937   -2.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2116   -3.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5472   -4.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3580   -4.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3626   -2.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5501   -2.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2234   -1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4116   -1.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9293   -1.8861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2644   -2.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0752   -2.7196    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
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4217578

   (5Z)-5-[(3-phenoxyphenyl)methylidene]-3-phenyl-2-sulfanylideneimidazolidin-4-one

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: 372.45

Molecular Weight (Monoisotopic): 372.0932

AlogP: 4.74

#Rotatable Bonds: 4

Polar Surface Area: 41.57

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.73

CX Basic pKa: ┄

CX LogP: 4.95

CX LogD: 4.95

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -1.07

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