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

ID: ALA4085078

PubChem CID: 89251662

Max Phase: Preclinical

Molecular Formula: C18H19N3O6S

Molecular Weight: 405.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1CCN(c2ccc(S(=O)(=O)Oc3cccc([N+](=O)[O-])c3)cc2)C1=O

Standard InChI:  InChI=1S/C18H19N3O6S/c1-2-10-19-11-12-20(18(19)22)14-6-8-17(9-7-14)28(25,26)27-16-5-3-4-15(13-16)21(23)24/h3-9,13H,2,10-12H2,1H3

Standard InChI Key:  CCAUROVLNWECRZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    9.4514   -6.2280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8641   -6.9379    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.2725   -6.2255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7454   -7.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7442   -8.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4523   -8.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1620   -8.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1591   -7.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4505   -6.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5767   -7.3402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2959   -6.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9883   -7.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7070   -6.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7310   -6.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0304   -5.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3146   -6.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0362   -8.5823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2926   -8.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7453   -8.8594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534   -9.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9528   -9.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1224   -7.4533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9327   -8.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4518   -9.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6392   -9.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0511   -4.9309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3539   -4.5046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7689   -4.5404    0.0000 O   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
 15 26  1  0
 26 27  1  0
 26 28  2  0
M  CHG  2  26   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4085078

   (3-Nitrophenyl) 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: 405.43

Molecular Weight (Monoisotopic): 405.0995

AlogP: 3.01

#Rotatable Bonds: 7

Polar Surface Area: 110.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: -1.74

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