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

ID: ALA4101980

PubChem CID: 71532462

Max Phase: Preclinical

Molecular Formula: C20H24N2O5S

Molecular Weight: 404.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN1CCN(c2ccc(S(=O)(=O)Oc3ccc(OC)cc3)cc2)C1=O

Standard InChI:  InChI=1S/C20H24N2O5S/c1-3-4-13-21-14-15-22(20(21)23)16-5-11-19(12-6-16)28(24,25)27-18-9-7-17(26-2)8-10-18/h5-12H,3-4,13-15H2,1-2H3

Standard InChI Key:  RBIXKTUNPPLTJH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.5269   -4.1479    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9353   -3.4355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4082   -4.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4070   -5.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1151   -5.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8247   -5.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8219   -4.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1133   -4.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2395   -4.5502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9587   -4.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6511   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3698   -4.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3938   -3.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6932   -2.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9774   -3.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6990   -5.7922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9554   -5.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4081   -6.0694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8162   -6.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6156   -6.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7852   -4.6633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955   -5.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1146   -6.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3020   -6.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9702   -5.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1125   -2.9977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8087   -3.4255    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
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  5 17  1  0
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 19 20  1  0
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 18 22  2  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 14 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101980

   (4-Methoxyphenyl) 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: 404.49

Molecular Weight (Monoisotopic): 404.1406

AlogP: 3.51

#Rotatable Bonds: 8

Polar Surface Area: 76.15

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: 3.40

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: -1.18

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