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

ID: ALA4089480

PubChem CID: 53372742

Max Phase: Preclinical

Molecular Formula: C19H22N2O4S

Molecular Weight: 374.46

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  ZUBGRDZEGNCAPK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.3370   -6.3229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7497   -7.0328    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1581   -6.3204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6310   -7.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6299   -8.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3379   -8.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0476   -8.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3361   -7.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4623   -7.4352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1815   -7.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8740   -7.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5927   -7.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6167   -6.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9161   -5.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2002   -6.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9219   -8.6772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1783   -8.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310   -8.9544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0391   -9.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8385   -9.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0081   -7.5482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183   -8.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -9.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5248   -9.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9367   -5.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  5  6  1  0
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  9  4  1  0
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  2 10  1  0
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  5 17  1  0
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 20 21  1  0
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 19 23  1  0
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 15 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089480

   (3-Methylphenyl) 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: 374.46

Molecular Weight (Monoisotopic): 374.1300

AlogP: 3.41

#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: 3.63

CX LogD: 3.63

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.73

Np Likeness Score: -1.56

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