(5Z)-3-(Naphth-1-yl)-5-(4-phenoxybenzylidene)-2-thioxoimidazolidin-4-one

ID: ALA4213821

PubChem CID: 145967015

Max Phase: Preclinical

Molecular Formula: C26H18N2O2S

Molecular Weight: 422.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2ccc(Oc3ccccc3)cc2)NC(=S)N1c1cccc2ccccc12

Standard InChI:  InChI=1S/C26H18N2O2S/c29-25-23(17-18-13-15-21(16-14-18)30-20-9-2-1-3-10-20)27-26(31)28(25)24-12-6-8-19-7-4-5-11-22(19)24/h1-17H,(H,27,31)/b23-17-

Standard InChI Key:  ZZBSRQUZLICZIS-QJOMJCCJSA-N

Molfile:  

     RDKit          2D

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   26.0304  -14.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.9631  -13.6480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6206  -12.3487    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.5100  -15.0864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0586  -13.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6136  -12.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   28.0962  -15.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8753  -15.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0440  -14.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4856  -14.7379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0053  -15.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1924  -15.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7122  -15.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0446  -16.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8618  -16.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3383  -16.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  8  1  0
  1 12  2  0
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 28 29  2  0
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 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4213821

   ---

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: 422.51

Molecular Weight (Monoisotopic): 422.1089

AlogP: 5.89

#Rotatable Bonds: 4

Polar Surface Area: 41.57

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.73

CX Basic pKa: ┄

CX LogP: 5.94

CX LogD: 5.94

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.33

Np Likeness Score: -0.89

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