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

ID: ALA5268914

Max Phase: Preclinical

Molecular Formula: C21H29N3O3S

Molecular Weight: 403.55

Names and Identifiers

Canonical SMILES:  CN1C(=S)N(C2CCCCC2)C(=O)/C1=C\c1ccc(N(C)CCCO)cc1O

Standard InChI:  InChI=1S/C21H29N3O3S/c1-22(11-6-12-25)17-10-9-15(19(26)14-17)13-18-20(27)24(21(28)23(18)2)16-7-4-3-5-8-16/h9-10,13-14,16,25-26H,3-8,11-12H2,1-2H3/b18-13+

Standard InChI Key:  DCZOFUZQBABTJT-QGOAFFKASA-N

Molfile:  

 
     RDKit          2D

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   -3.1109   -0.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3963    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6819   -0.3416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6819   -1.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9675    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585    0.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585    0.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1730    1.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8874    0.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0659    0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4826   -0.4846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8898    0.0064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3024   -0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8898   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1273   -2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5397   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1273   -0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2205    0.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174    0.9543    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6019    1.3120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6019    2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    1.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9675    0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    2.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5397   -0.3416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  4  5  1  0
  6  4  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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 15 14  1  0
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 17 18  1  0
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 19 20  1  0
 15 20  1  0
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 23 21  1  0
 23 11  1  0
 23 24  1  0
  9 25  1  0
 26  6  1  0
 25 26  2  0
 25 27  1  0
  1 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5268914

   ---

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: 403.55

Molecular Weight (Monoisotopic): 403.1930

AlogP: 2.94

#Rotatable Bonds: 6

Polar Surface Area: 67.25

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.27

CX Basic pKa: 3.94

CX LogP: 2.99

CX LogD: 2.98

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -0.73

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