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

ID: ALA4087822

PubChem CID: 137642057

Max Phase: Preclinical

Molecular Formula: C18H20N2O5S

Molecular Weight: 376.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H20N2O5S/c1-3-19-11-12-20(18(19)21)14-7-9-17(10-8-14)26(22,23)25-16-6-4-5-15(13-16)24-2/h4-10,13H,3,11-12H2,1-2H3

Standard InChI Key:  WPYFMVFIWMXCDZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    8.5516   -5.0435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9643   -5.7534    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.3728   -5.0410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8457   -6.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8445   -6.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5526   -7.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2622   -6.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2594   -6.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5508   -5.7613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6770   -6.1557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3962   -5.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0886   -6.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8073   -5.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8313   -4.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1307   -4.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4149   -4.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1365   -7.3977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3929   -7.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8456   -7.6749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2537   -8.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0531   -8.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2227   -6.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0330   -7.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5521   -8.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1514   -3.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8692   -3.3558    0.0000 C   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
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087822

   ---

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: 376.43

Molecular Weight (Monoisotopic): 376.1093

AlogP: 2.72

#Rotatable Bonds: 6

Polar Surface Area: 76.15

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.43

CX LogD: 2.43

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -1.30

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