3,4,5-Trimethoxyphenyl-4-(2-Oxo-3-propylimidazolidin-1-yl)benzenesulfonate

ID: ALA4096550

PubChem CID: 71511831

Max Phase: Preclinical

Molecular Formula: C21H26N2O7S

Molecular Weight: 450.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1CCN(c2ccc(S(=O)(=O)Oc3cc(OC)c(OC)c(OC)c3)cc2)C1=O

Standard InChI:  InChI=1S/C21H26N2O7S/c1-5-10-22-11-12-23(21(22)24)15-6-8-17(9-7-15)31(25,26)30-16-13-18(27-2)20(29-4)19(14-16)28-3/h6-9,13-14H,5,10-12H2,1-4H3

Standard InChI Key:  RGHUBNVNRBTODR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
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    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
   11.3412   -5.4551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0590   -5.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6926   -7.9477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6686   -8.7645    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
   13.4360   -6.7397    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
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  2 10  1  0
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  5 17  1  0
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 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 18 22  2  0
 19 23  1  0
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 24 25  1  0
 15 26  1  0
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 13 28  1  0
 28 29  1  0
 14 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096550

   (3,4,5-Trimethoxyphenyl) 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: 450.51

Molecular Weight (Monoisotopic): 450.1461

AlogP: 3.13

#Rotatable Bonds: 9

Polar Surface Area: 94.61

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.64

CX LogD: 2.64

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: -0.92

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