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

ID: ALA5271584

Max Phase: Preclinical

Molecular Formula: C21H23N3O3S

Molecular Weight: 397.50

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H23N3O3S/c1-22(11-12-25)17-10-9-15(19(14-17)27-3)13-18-20(26)24(21(28)23(18)2)16-7-5-4-6-8-16/h4-10,13-14,25H,11-12H2,1-3H3/b18-13+

Standard InChI Key:  PWMRZQQUPHANSG-QGOAFFKASA-N

Molfile:  

 
     RDKit          2D

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   -0.6104    1.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1013   -0.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6087   -0.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -0.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397   -0.5477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397   -1.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -0.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159    1.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5306    0.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    1.1063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8639    0.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333   -0.1995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7091   -0.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    1.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1256   -0.6907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6610    0.7486    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459   -0.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -0.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1836   -1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -2.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459   -2.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333   -1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4689   -0.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1836   -0.1351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104    1.9308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3251    2.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
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 19 24  2  0
 24 23  1  0
  9 25  1  0
 25 26  1  0
  2 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5271584

   ---

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: 397.50

Molecular Weight (Monoisotopic): 397.1460

AlogP: 2.73

#Rotatable Bonds: 6

Polar Surface Area: 56.25

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.03

CX LogP: 2.93

CX LogD: 2.93

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: -1.19

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