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

ID: ALA4215753

PubChem CID: 98103582

Max Phase: Preclinical

Molecular Formula: C17H14N2O2S

Molecular Weight: 310.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(/C=C2\NC(=S)N(c3ccccc3)C2=O)c1

Standard InChI:  InChI=1S/C17H14N2O2S/c1-21-14-9-5-6-12(10-14)11-15-16(20)19(17(22)18-15)13-7-3-2-4-8-13/h2-11H,1H3,(H,18,22)/b15-11-

Standard InChI Key:  MWWTVXPXKVNFDK-PTNGSMBKSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    4.7339  -15.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5511  -15.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8055  -14.5106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1425  -14.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4838  -14.5106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1412  -13.2113    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0307  -15.9490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792  -14.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1857  -14.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9626  -14.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1343  -13.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5228  -13.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7483  -13.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2527  -15.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401  -15.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1129  -15.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3011  -15.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8190  -15.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1545  -16.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9654  -16.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9700  -14.2779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4515  -13.6176    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
M  END

Alternative Forms

1. Parent:

   

   ALA4215753

   5-(3-Methoxybenzylidene)-3-phenyl-2-thioxoimidazolidin-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: 310.38

Molecular Weight (Monoisotopic): 310.0776

AlogP: 2.96

#Rotatable Bonds: 3

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: 3.29

CX LogD: 3.29

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.70

Np Likeness Score: -1.24

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