5-[[4-(1-Naphthylacetoxy)phenyl]methyl]-2-thioxo-4-imidazolidinone

ID: ALA2272111

PubChem CID: 76323418

Max Phase: Preclinical

Molecular Formula: C22H18N2O3S

Molecular Weight: 390.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1cccc2ccccc12)Oc1ccc(CC2NC(=S)NC2=O)cc1

Standard InChI:  InChI=1S/C22H18N2O3S/c25-20(13-16-6-3-5-15-4-1-2-7-18(15)16)27-17-10-8-14(9-11-17)12-19-21(26)24-22(28)23-19/h1-11,19H,12-13H2,(H2,23,24,26,28)

Standard InChI Key:  VMQFAPJWYMVQGW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   17.0056  -12.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7203  -13.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4368  -12.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4340  -12.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7185  -11.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1468  -11.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8629  -12.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9559  -12.8765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7635  -13.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1733  -12.3290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6189  -11.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2908  -13.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5767  -12.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8618  -13.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5773  -12.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7876  -10.9105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1019  -13.7974    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.8612  -14.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8589  -15.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5761  -15.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5735  -14.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1442  -15.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1473  -14.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4368  -14.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7227  -14.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7236  -15.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4347  -15.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12 17  2  0
 10 18  2  0
 15 19  1  0
 19 24  2  0
 23 20  2  0
 20 21  1  0
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 22 19  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2272111

   [4-[(5-Oxo-2-sulfanylideneimidazolidin-4-yl)methyl]phenyl] 2-naphthalen-1-ylacetate

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: 390.46

Molecular Weight (Monoisotopic): 390.1038

AlogP: 2.90

#Rotatable Bonds: 5

Polar Surface Area: 67.43

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.64

CX Basic pKa: ┄

CX LogP: 4.10

CX LogD: 4.09

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: -0.38

References

1. Han J, Wang J, Dong H, Lei J, Wang M, Fang J..  (2011)  Synthesis and herbicidal activity of 5-(4-hydroxybenzyl)-2-thioxoimidazolidin-4-one esters.,  16  (4): [PMID:21455096] [10.3390/molecules16042833]

Source

Source(1):

• Scientific Literature