3,4,5-Trimethoxyphenyl-4-(3-Ethyl-2-oxoimidazolidin-1-yl)benzenesulfonate

ID: ALA4094460

PubChem CID: 137653073

Max Phase: Preclinical

Molecular Formula: C20H24N2O7S

Molecular Weight: 436.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CCN(c2ccc(S(=O)(=O)Oc3cc(OC)c(OC)c(OC)c3)cc2)C1=O

Standard InChI:  InChI=1S/C20H24N2O7S/c1-5-21-10-11-22(20(21)23)14-6-8-16(9-7-14)30(24,25)29-15-12-17(26-2)19(28-4)18(13-15)27-3/h6-9,12-13H,5,10-11H2,1-4H3

Standard InChI Key:  RSFAXERMHJKOCE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.8335   -5.5140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2462   -6.2239    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6546   -5.5115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1275   -6.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1264   -7.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8344   -7.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5441   -7.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5412   -6.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8326   -6.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9588   -6.6262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6780   -6.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3705   -6.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0892   -6.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1132   -5.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4126   -5.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6967   -5.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4183   -7.8682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6748   -7.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1275   -8.1454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5355   -8.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349   -8.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5045   -6.7393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -8.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8340   -8.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4332   -4.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1510   -3.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7846   -6.7095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7606   -7.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8318   -5.0736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5281   -5.5015    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
 13 27  1  0
 27 28  1  0
 14 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094460

   ---

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: 436.49

Molecular Weight (Monoisotopic): 436.1304

AlogP: 2.74

#Rotatable Bonds: 8

Polar Surface Area: 94.61

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.12

CX LogD: 2.12

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.59

Np Likeness Score: -0.88

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