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

ID: ALA3274646

PubChem CID: 12381190

Max Phase: Preclinical

Molecular Formula: C17H22N4O5S

Molecular Weight: 394.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c([N+](=O)[O-])cnc1SCCCCCCCOc1ccccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C17H22N4O5S/c1-19-16(21(24)25)13-18-17(19)27-12-8-4-2-3-7-11-26-15-10-6-5-9-14(15)20(22)23/h5-6,9-10,13H,2-4,7-8,11-12H2,1H3

Standard InChI Key:  NCBGSBHHTSMTJX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   11.4022   -6.0579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1188   -6.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8149   -6.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5310   -6.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5495   -7.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8459   -7.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1328   -7.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -6.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1224   -7.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219   -7.1330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0254   -6.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896   -5.9796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5160   -7.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7419   -5.9332    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4405   -6.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1570   -5.9644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8556   -6.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5721   -5.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7722   -8.0238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356   -8.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576   -8.0886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2706   -6.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9872   -6.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6857   -6.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7963   -5.2040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0790   -4.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4940   -4.7786    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
M  CHG  4  19   1  21  -1  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3274646

   1-Methyl-5-nitro-2-[7-(2-nitrophenoxy)heptylsulfanyl]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: 394.45

Molecular Weight (Monoisotopic): 394.1311

AlogP: 4.36

#Rotatable Bonds: 12

Polar Surface Area: 113.33

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.06

CX LogP: 4.81

CX LogD: 4.81

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.23

Np Likeness Score: -1.48

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