3-Chlorophenyl-4-(3-Ethyl-2-oxoimidazolidin-1-yl)benzenesulfonate

ID: ALA4093547

PubChem CID: 123719406

Max Phase: Preclinical

Molecular Formula: C17H17ClN2O4S

Molecular Weight: 380.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CCN(c2ccc(S(=O)(=O)Oc3cccc(Cl)c3)cc2)C1=O

Standard InChI:  InChI=1S/C17H17ClN2O4S/c1-2-19-10-11-20(17(19)21)14-6-8-16(9-7-14)25(22,23)24-15-5-3-4-13(18)12-15/h3-9,12H,2,10-11H2,1H3

Standard InChI Key:  FHHOHSLWUFMTMX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    7.7138   -5.0146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1265   -5.7245    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5349   -5.0121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0078   -6.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0067   -6.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7147   -7.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4244   -6.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -6.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7129   -5.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8391   -6.1268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5583   -5.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2508   -6.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9695   -5.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9935   -4.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2929   -4.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5770   -4.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2987   -7.3689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5551   -7.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0078   -7.6460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4158   -8.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2153   -8.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3849   -6.2399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1951   -7.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7143   -8.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3135   -3.7175    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8  2  1  0
  2 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 18 22  2  0
 19 23  1  0
 23 24  1  0
 15 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093547

   ---

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: 380.85

Molecular Weight (Monoisotopic): 380.0598

AlogP: 3.37

#Rotatable Bonds: 5

Polar Surface Area: 66.92

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.19

CX LogD: 3.19

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: -1.68

References

1. Fortin S, Charest-Morin X, Turcotte V, Lauvaux C, Lacroix J, Côté MF, Gobeil S, C-Gaudreault R..  (2017)  Activation of Phenyl 4-(2-Oxo-3-alkylimidazolidin-1-yl)benzenesulfonates Prodrugs by CYP1A1 as New Antimitotics Targeting Breast Cancer Cells.,  60  (12): [PMID:28535350] [10.1021/acs.jmedchem.7b00343]

Source

Source(1):

• Scientific Literature