ethyl 4-(6-(1-methyl-5-nitro-1H-imidazol-2-ylthio)hexyloxy)-3-nitrobenzoate

ID: ALA3274645

PubChem CID: 12381189

Max Phase: Preclinical

Molecular Formula: C19H24N4O7S

Molecular Weight: 452.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(OCCCCCCSc2ncc([N+](=O)[O-])n2C)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C19H24N4O7S/c1-3-29-18(24)14-8-9-16(15(12-14)22(25)26)30-10-6-4-5-7-11-31-19-20-13-17(21(19)2)23(27)28/h8-9,12-13H,3-7,10-11H2,1-2H3

Standard InChI Key:  YMQCWKXXUWRTFN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.2865   -4.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0030   -3.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6992   -4.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4152   -3.7056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4337   -2.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7302   -2.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0170   -2.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1506   -2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8497   -2.9142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1675   -1.6741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -4.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -4.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5216   -4.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6251   -3.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8892   -3.5941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1157   -5.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3416   -3.5476    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0401   -3.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7567   -3.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4552   -4.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1717   -3.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3719   -5.6383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8353   -6.3114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5573   -5.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8703   -4.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5868   -3.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3128   -2.4366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5980   -2.8326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3273   -1.6196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5657   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2648   -2.9436    0.0000 C   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
  8  9  1  0
  8 10  2  0
  5  8  1  0
 12 13  1  0
 11 12  2  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
 13 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 22 23  2  0
 22 24  1  0
 12 22  1  0
 21 25  1  0
 25 26  1  0
 26  1  1  0
 27 28  2  0
 27 29  1  0
  7 27  1  0
  9 30  1  0
 30 31  1  0
M  CHG  4  22   1  24  -1  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3274645

   Ethyl 4-[6-(1-methyl-5-nitroimidazol-2-yl)sulfanylhexoxy]-3-nitrobenzoate

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: 452.49

Molecular Weight (Monoisotopic): 452.1366

AlogP: 4.14

#Rotatable Bonds: 13

Polar Surface Area: 139.63

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 1.06

CX LogP: 4.73

CX LogD: 4.73

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.14

Np Likeness Score: -1.41

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