(E)-5-(4-(dimethylamino)-2-methoxybenzylidene)-1-methyl-3-phenyl-2-thioxoimidazolidin-4-one

ID: ALA5282245

Max Phase: Preclinical

Molecular Formula: C20H21N3O2S

Molecular Weight: 367.47

Names and Identifiers

Canonical SMILES:  COc1cc(N(C)C)ccc1/C=C1\C(=O)N(c2ccccc2)C(=S)N1C

Standard InChI:  InChI=1S/C20H21N3O2S/c1-21(2)16-11-10-14(18(13-16)25-4)12-17-19(24)23(20(26)22(17)3)15-8-6-5-7-9-15/h5-13H,1-4H3/b17-12+

Standard InChI Key:  CWJPOARFKDXYGC-SFQUDFHCSA-N

Molfile:  

 
     RDKit          2D

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   -1.3251    1.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132    0.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132   -0.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233   -0.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397   -0.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -0.5477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -1.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690   -0.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013    1.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159    0.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    1.1063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1493    0.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186   -0.1995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945   -0.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    1.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4109   -0.6907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9464    0.7485    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2312   -0.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0564   -0.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4690   -1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0564   -2.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2312   -2.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186   -1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3251    1.9308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397    2.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA5282245

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 367.47

Molecular Weight (Monoisotopic): 367.1354

AlogP: 3.37

#Rotatable Bonds: 4

Polar Surface Area: 36.02

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.61

CX LogP: 3.62

CX LogD: 3.62

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: -1.14

References

1. Shim S, Jeong DU, Kim H, Kim CY, Park H, Jin Y, Kim KM, Lee HJ, Kim DH, Bae YS, Choi Y..  (2022)  Discovery of a NADPH oxidase inhibitor, (E)-3-cyclohexyl-5-(4-((2-hydroxyethyl)(methyl)amino)benzylidene)-1-methyl-2-thioxoimidazolidin-4-oneone, as a novel therapeutic for Parkinson's disease.,  244  [PMID:36274279] [10.1016/j.ejmech.2022.114854]

Source

Source(1):

• Scientific Literature