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

ID: ALA2272134

PubChem CID: 76312562

Max Phase: Preclinical

Molecular Formula: C17H13N3O5S

Molecular Weight: 371.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Oc1ccc(CC2NC(=S)NC2=O)cc1)c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C17H13N3O5S/c21-15-14(18-17(26)19-15)9-10-1-7-13(8-2-10)25-16(22)11-3-5-12(6-4-11)20(23)24/h1-8,14H,9H2,(H2,18,19,21,26)

Standard InChI Key:  MOVNAXLBEMWACZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    5.6736  -26.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6724  -27.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3872  -27.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1036  -27.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1008  -26.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854  -26.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8137  -26.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5297  -26.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6227  -27.3723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4303  -27.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8402  -26.8247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2857  -26.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9576  -27.8016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2434  -27.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287  -27.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2441  -26.5636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4544  -25.4063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7687  -28.2932    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8152  -27.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1010  -27.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0999  -28.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8191  -29.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304  -28.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834  -29.0331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838  -29.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6730  -28.6210    0.0000 O   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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 15  1  0
 24 25  2  0
 24 26  1  0
 21 24  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2272134

   [4-[(5-Oxo-2-sulfanylideneimidazolidin-4-yl)methyl]phenyl] 4-nitrobenzoate

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: 371.37

Molecular Weight (Monoisotopic): 371.0576

AlogP: 1.73

#Rotatable Bonds: 5

Polar Surface Area: 110.57

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.64

CX Basic pKa: ┄

CX LogP: 3.27

CX LogD: 3.26

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.27

Np Likeness Score: -0.61

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