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

ID: ALA4104279

PubChem CID: 88909651

Max Phase: Preclinical

Molecular Formula: C19H22N2O5S

Molecular Weight: 390.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1CCN(c2ccc(S(=O)(=O)Oc3ccc(OC)cc3)cc2)C1=O

Standard InChI:  InChI=1S/C19H22N2O5S/c1-3-12-20-13-14-21(19(20)22)15-4-10-18(11-5-15)27(23,24)26-17-8-6-16(25-2)7-9-17/h4-11H,3,12-14H2,1-2H3

Standard InChI Key:  HBSMNUTUYZOFES-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    9.1542   -7.4620    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5626   -6.7497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0355   -7.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0344   -8.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7424   -9.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4521   -8.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4492   -7.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7406   -7.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8668   -7.8644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5860   -7.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2785   -7.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9971   -7.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0212   -6.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3205   -6.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6047   -6.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3263   -9.1064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5827   -8.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0355   -9.3836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4435  -10.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2429   -9.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4125   -7.9775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2228   -9.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7420   -9.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9293   -9.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7398   -6.3118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7623   -5.4949    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
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 12 13  1  0
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  5 17  1  0
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 18 19  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
 14 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4104279

   (4-Methoxyphenyl) 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: 390.46

Molecular Weight (Monoisotopic): 390.1249

AlogP: 3.11

#Rotatable Bonds: 7

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: 2.96

CX LogD: 2.96

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: -1.23

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