3-Fluorophenyl-4-(2-Oxo-3-propylimidazolidin-1-yl)benzenesulfonate

ID: ALA4097180

PubChem CID: 88909660

Max Phase: Preclinical

Molecular Formula: C18H19FN2O4S

Molecular Weight: 378.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1CCN(c2ccc(S(=O)(=O)Oc3cccc(F)c3)cc2)C1=O

Standard InChI:  InChI=1S/C18H19FN2O4S/c1-2-10-20-11-12-21(18(20)22)15-6-8-17(9-7-15)26(23,24)25-16-5-3-4-14(19)13-16/h3-9,13H,2,10-12H2,1H3

Standard InChI Key:  SZNVNJGEOPBZBC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    8.3700   -6.6902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7827   -7.4001    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1912   -6.6878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6641   -7.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6629   -8.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3710   -9.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0806   -8.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0778   -7.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3692   -7.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4954   -7.8025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2146   -7.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9070   -7.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6257   -7.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6497   -6.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9491   -6.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2333   -6.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9549   -9.0445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2113   -8.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6640   -9.3217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0721  -10.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8715   -9.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0411   -7.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8514   -9.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3705   -9.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -9.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9698   -5.3932    0.0000 F   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
 24 25  1  0
 15 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097180

   (3-Fluorophenyl) 4-(2-oxo-3-propylimidazolidin-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: 378.43

Molecular Weight (Monoisotopic): 378.1050

AlogP: 3.25

#Rotatable Bonds: 6

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: 3.26

CX LogD: 3.26

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -1.76

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