1-methyl-5-nitro-2-(7-(2-nitrophenoxy)heptylsulfinyl)-1H-imidazole

ID: ALA3274647

PubChem CID: 12381191

Max Phase: Preclinical

Molecular Formula: C17H22N4O6S

Molecular Weight: 410.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c([N+](=O)[O-])cnc1[S+]([O-])CCCCCCCOc1ccccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C17H22N4O6S/c1-19-16(21(24)25)13-18-17(19)28(26)12-8-4-2-3-7-11-27-15-10-6-5-9-14(15)20(22)23/h5-6,9-10,13H,2-4,7-8,11-12H2,1H3

Standard InChI Key:  JEGFARDNTLHTSU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    3.9999   -8.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2642   -9.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -8.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8301   -9.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7955   -9.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5021  -10.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2343   -9.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7804   -9.3443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3726  -10.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5633   -9.8952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4736   -9.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2279   -8.7355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9489  -10.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7531   -8.6604    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0353   -9.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3148   -8.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5969   -9.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8765   -8.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7142  -10.8224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2304  -11.4974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5406  -10.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1586   -9.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4381   -8.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7203   -9.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999   -7.7839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362   -7.3999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8992   -7.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7505   -7.8300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  9 10  1  0
  8  9  2  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 10 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 20  2  0
 19 21  1  0
  9 19  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 24  1  1  0
 25 26  2  0
 25 27  1  0
  3 25  1  0
 14 28  1  0
M  CHG  6  14   1  19   1  21  -1  25   1  27  -1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3274647

   1-Methyl-5-nitro-2-[7-(2-nitrophenoxy)heptylsulfinyl]imidazole

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: 410.45

Molecular Weight (Monoisotopic): 410.1260

AlogP: 3.37

#Rotatable Bonds: 12

Polar Surface Area: 136.39

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.23

Np Likeness Score: -0.79

References

1. Tweit RC, Muir RD, Ziecina S..  (1977)  Nitroimidazoles with antibacterial activity against Neisseria gonorrhoeae.,  20  (12): [PMID:412966] [10.1021/jm00222a036]

Source

Source(1):

• Scientific Literature