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

ID: ALA4085801

PubChem CID: 137641732

Max Phase: Preclinical

Molecular Formula: C17H17IN2O4S

Molecular Weight: 472.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H17IN2O4S/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:  YKCYDXIJRFFAQC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    8.2999   -7.1773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7126   -7.8871    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1210   -7.1748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5939   -8.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5927   -9.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008   -9.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0105   -9.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0076   -8.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2990   -7.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4252   -8.2895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1444   -7.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8369   -8.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5555   -7.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5795   -7.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8789   -6.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1631   -7.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8847   -9.5315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1411   -9.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5938   -9.8087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0019  -10.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8013  -10.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709   -8.4026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7812   -9.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3003  -10.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8996   -5.8802    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
 23 24  1  0
 15 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085801

   ---

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: 472.30

Molecular Weight (Monoisotopic): 471.9954

AlogP: 3.32

#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: 3.52

CX LogD: 3.52

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.49

Np Likeness Score: -1.69

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