3-(4-Ethylphenyl)-5-(4-(N,N-dimethylamino)benzylidene)-1-methyl-2-thiohydantoin

ID: ALA3827342

PubChem CID: 127045604

Max Phase: Preclinical

Molecular Formula: C21H23N3OS

Molecular Weight: 365.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(N2C(=O)/C(=C/c3ccc(N(C)C)cc3)N(C)C2=S)cc1

Standard InChI:  InChI=1S/C21H23N3OS/c1-5-15-6-12-18(13-7-15)24-20(25)19(23(4)21(24)26)14-16-8-10-17(11-9-16)22(2)3/h6-14H,5H2,1-4H3/b19-14-

Standard InChI Key:  FEQBFJABEFHTOQ-RGEXLXHISA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056   -3.8679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372   -5.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0391   -6.2662    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -5.2877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786   -3.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2409   -3.4780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460   -3.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8976   -0.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019    0.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2031    1.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4999    0.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4957   -0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8034    1.4829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8400    0.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    2.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508   -6.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4504   -7.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4759   -9.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989   -8.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -7.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248   -6.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -9.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558   -9.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  1  6  1  0
  2  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 16 17  1  0
 16 18  1  0
 13 16  1  0
  1  9  2  0
  5 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3827342

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 365.50

Molecular Weight (Monoisotopic): 365.1562

AlogP: 3.92

#Rotatable Bonds: 4

Polar Surface Area: 26.79

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.54

CX LogP: 4.74

CX LogD: 4.74

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: -1.16

References

1. Bae YS, Choi S, Park JJ, Joo JH, Cui M, Cho H, Lee WJ, Lee SH..  (2016)  Synthesis and biological evaluation of 3-substituted 5-benzylidene-1-methyl-2-thiohydantoins as potent NADPH oxidase (NOX) inhibitors.,  24  (18): [PMID:27407031] [10.1016/j.bmc.2016.06.056]

Source

Source(1):

• Scientific Literature