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

ID: ALA5287582

Max Phase: Preclinical

Molecular Formula: C22H25N3O3S

Molecular Weight: 411.53

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H25N3O3S/c1-23(12-7-13-26)18-11-10-16(20(15-18)28-3)14-19-21(27)25(22(29)24(19)2)17-8-5-4-6-9-17/h4-6,8-11,14-15,26H,7,12-13H2,1-3H3/b19-14+

Standard InChI Key:  UUFRGRCHCSZSNP-XMHGGMMESA-N

Molfile:  

 
     RDKit          2D

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    0.4586   -0.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513   -0.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -0.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824   -0.5477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824   -1.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6025    1.1063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213    0.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -0.1995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0663   -0.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025    1.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827   -0.6907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0184    0.7485    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1284   -0.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5409   -1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1283   -2.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -2.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1116   -0.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8263   -0.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5409   -0.5477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    1.9308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678    2.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 10  1  0
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 19 14  1  0
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 21 20  2  0
 22 21  1  0
 23 22  2  0
 19 24  2  0
 24 23  1  0
  9 25  1  0
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 26 27  1  0
  2 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287582

   ---

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: 411.53

Molecular Weight (Monoisotopic): 411.1617

AlogP: 3.12

#Rotatable Bonds: 7

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: 3.91

CX LogP: 2.99

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: -1.11

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