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

ID: ALA4101885

PubChem CID: 137661515

Max Phase: Preclinical

Molecular Formula: C19H22N2O4S

Molecular Weight: 374.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN1CCN(c2ccc(S(=O)(=O)Oc3ccccc3)cc2)C1=O

Standard InChI:  InChI=1S/C19H22N2O4S/c1-2-3-13-20-14-15-21(19(20)22)16-9-11-18(12-10-16)26(23,24)25-17-7-5-4-6-8-17/h4-12H,2-3,13-15H2,1H3

Standard InChI Key:  UMNGJWMRSDXZLA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.6754   -5.6089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0882   -6.3188    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4966   -5.6064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9695   -6.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9683   -7.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6764   -7.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3860   -7.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3832   -6.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6746   -6.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8008   -6.7211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5200   -6.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2124   -6.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9311   -6.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9551   -5.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2545   -5.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5387   -5.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -7.9632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -7.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9694   -8.2404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3775   -8.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1769   -8.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3465   -6.8342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1568   -8.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6759   -8.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8633   -8.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5315   -7.9822    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
 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
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101885

   ---

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: 374.46

Molecular Weight (Monoisotopic): 374.1300

AlogP: 3.50

#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: 3.56

CX LogD: 3.56

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -1.33

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