(5Z)-5-(4-Hydroxy-3-methoxybenzylidene)-3-phenyl-2-thioxoimidazolidin-4-one

ID: ALA4208777

Cas Number: 325994-26-1

PubChem CID: 684753

Max Phase: Preclinical

Molecular Formula: C17H14N2O3S

Molecular Weight: 326.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\NC(=S)N(c3ccccc3)C2=O)ccc1O

Standard InChI:  InChI=1S/C17H14N2O3S/c1-22-15-10-11(7-8-14(15)20)9-13-16(21)19(17(23)18-13)12-5-3-2-4-6-12/h2-10,20H,1H3,(H,18,23)/b13-9-

Standard InChI Key:  KMDMVAOTISXADM-LCYFTJDESA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   14.0284   -3.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8456   -3.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1000   -2.7521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4370   -2.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7783   -2.7521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4358   -1.4528    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.3252   -4.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8738   -2.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4802   -3.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2571   -2.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4288   -1.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8173   -1.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0428   -1.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5472   -4.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7346   -4.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4074   -3.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5956   -3.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1135   -3.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4490   -4.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2599   -4.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2645   -2.5194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7460   -1.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3008   -3.8421    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA4208777

   5-(4-Hydroxy-3-methoxybenzylidene)-2-mercapto-3-phenyl-3,5-dihydro-4H-imidazol-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: 326.38

Molecular Weight (Monoisotopic): 326.0725

AlogP: 2.66

#Rotatable Bonds: 3

Polar Surface Area: 61.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: ┄

CX LogP: 2.99

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.67

Np Likeness Score: -0.69

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