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

ID: ALA5287636

Max Phase: Preclinical

Molecular Formula: C21H23N3O2S

Molecular Weight: 381.50

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H23N3O2S/c1-22(13-6-14-25)17-11-9-16(10-12-17)15-19-20(26)24(21(27)23(19)2)18-7-4-3-5-8-18/h3-5,7-12,15,25H,6,13-14H2,1-2H3/b19-15+

Standard InChI Key:  ARHDQQCWGCPBFW-XDJHFCHBSA-N

Molfile:  

 
     RDKit          2D

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   -0.2532    1.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4587    0.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4587    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824   -0.3418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824   -1.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3969    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732    1.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879    0.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025    1.3122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906    0.0064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0663    0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025    2.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827   -0.4847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0183    0.9545    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032   -0.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1283   -0.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5409   -1.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1283   -2.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032   -2.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -1.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1117   -0.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8263    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5409   -0.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  4  3  2  0
  5  4  1  0
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  3 10  1  0
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 15 17  2  0
 13 18  2  0
 19 14  1  0
 19 20  1  0
 21 20  2  0
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 23 22  2  0
 19 24  2  0
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  9 25  1  0
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 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287636

   ---

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: 381.50

Molecular Weight (Monoisotopic): 381.1511

AlogP: 3.11

#Rotatable Bonds: 6

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: 4.72

CX LogP: 3.15

CX LogD: 3.15

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: -1.12

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