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

ID: ALA4085455

PubChem CID: 71532407

Max Phase: Preclinical

Molecular Formula: C19H21FN2O4S

Molecular Weight: 392.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H21FN2O4S/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:  MYRFIBIEBAHRQE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.2132   -5.0476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6259   -5.7575    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0343   -5.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5072   -6.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5061   -6.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2141   -7.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9238   -6.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9210   -6.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2123   -5.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3385   -6.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0577   -5.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7502   -6.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4689   -5.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4929   -4.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7923   -4.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0764   -4.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7980   -7.4019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0545   -7.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072   -7.6791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9152   -8.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7146   -8.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8843   -6.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945   -7.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2137   -8.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010   -8.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0692   -7.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1643   -6.2431    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
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 15 16  2  0
 16 11  1  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
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 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:

   

   ALA4085455

   (3-Fluorophenyl) 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: 392.45

Molecular Weight (Monoisotopic): 392.1206

AlogP: 3.64

#Rotatable Bonds: 7

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: 3.70

CX LogD: 3.70

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: -1.68

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