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

ID: ALA5291222

Max Phase: Preclinical

Molecular Formula: C20H21N3O2S

Molecular Weight: 367.47

Names and Identifiers

Canonical SMILES:  CN1C(=S)N(c2ccccc2)C(=O)/C1=C\c1ccc(N(C)CCO)cc1

Standard InChI:  InChI=1S/C20H21N3O2S/c1-21(12-13-24)16-10-8-15(9-11-16)14-18-19(25)23(20(26)22(18)2)17-6-4-3-5-7-17/h3-11,14,24H,12-13H2,1-2H3/b18-14+

Standard InChI Key:  CNGIFXJOIFIXBT-NBVRZTHBSA-N

Molfile:  

 
     RDKit          2D

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   -0.6103    1.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012    0.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1012    0.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8158    1.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5304    0.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2449    1.3120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8636    0.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5328    0.0063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7088    0.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2449    2.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254   -0.4846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605    0.9543    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9455   -0.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7705   -0.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831   -1.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7705   -2.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9454   -2.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5328   -1.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4685   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1831    0.0707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  9 25  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA5291222

   ---

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: 2.72

#Rotatable Bonds: 5

Polar Surface Area: 47.02

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.88

CX LogP: 3.09

CX LogD: 3.09

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.65

Np Likeness Score: -1.21

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