3,4-Dimethoxyphenyl-4-(3-Ethyl-2-oxoimidazolidin-1-yl)benzenesulfonate

ID: ALA4102196

PubChem CID: 137660342

Max Phase: Preclinical

Molecular Formula: C19H22N2O6S

Molecular Weight: 406.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CCN(c2ccc(S(=O)(=O)Oc3ccc(OC)c(OC)c3)cc2)C1=O

Standard InChI:  InChI=1S/C19H22N2O6S/c1-4-20-11-12-21(19(20)22)14-5-8-16(9-6-14)28(23,24)27-15-7-10-17(25-2)18(13-15)26-3/h5-10,13H,4,11-12H2,1-3H3

Standard InChI Key:  ZELUCXHEYDYFPD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.3712   -5.5718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7840   -6.2816    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1924   -5.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6653   -6.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6641   -7.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3722   -7.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0818   -7.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0790   -6.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3704   -6.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4966   -6.6840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2158   -6.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9082   -6.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6269   -6.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6509   -5.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9503   -5.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2345   -5.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9561   -7.9260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -7.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6652   -8.2032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0733   -8.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727   -8.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0423   -6.7971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -8.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717   -8.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9710   -4.2747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3696   -5.1314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6888   -3.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3921   -4.3145    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
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  5 17  1  0
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 19 20  1  0
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 18 22  2  0
 19 23  1  0
 23 24  1  0
 15 25  1  0
 14 26  1  0
 25 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102196

   ---

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: 406.46

Molecular Weight (Monoisotopic): 406.1199

AlogP: 2.73

#Rotatable Bonds: 7

Polar Surface Area: 85.38

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.66

Np Likeness Score: -1.10

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