3-Iodophenyl-4-(3-Butyl-2-oxoimidazolidin-1-yl)-benzenesulfonate

ID: ALA4099490

PubChem CID: 71532409

Max Phase: Preclinical

Molecular Formula: C19H21IN2O4S

Molecular Weight: 500.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN1CCN(c2ccc(S(=O)(=O)Oc3cccc(I)c3)cc2)C1=O

Standard InChI:  InChI=1S/C19H21IN2O4S/c1-2-3-11-21-12-13-22(19(21)23)16-7-9-18(10-8-16)27(24,25)26-17-6-4-5-15(20)14-17/h4-10,14H,2-3,11-13H2,1H3

Standard InChI Key:  BVJUDQUCVHUSRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.1471   -3.6815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5599   -4.3914    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9683   -3.6790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4412   -4.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4400   -5.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1481   -6.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8577   -5.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8549   -4.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1463   -4.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2725   -4.7937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9917   -4.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6841   -4.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4028   -4.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4268   -3.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7262   -3.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0104   -3.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7320   -6.0358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9884   -5.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411   -6.3129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8492   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6486   -6.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8182   -4.9068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285   -6.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1476   -6.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3350   -6.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032   -6.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0983   -4.8770    0.0000 I   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
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 24 25  1  0
 25 26  1  0
 13 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099490

   (3-Iodophenyl) 4-(3-butyl-2-oxoimidazolidin-1-yl)benzenesulfonate

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: 500.36

Molecular Weight (Monoisotopic): 500.0267

AlogP: 4.10

#Rotatable Bonds: 7

Polar Surface Area: 66.92

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.49

CX LogD: 4.49

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.42

Np Likeness Score: -1.63

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