2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-methyl-4-nitrobenzoate

ID: ALA4100978

PubChem CID: 52467213

Max Phase: Preclinical

Molecular Formula: C14H14N4O6

Molecular Weight: 334.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C(=O)OCCn2c([N+](=O)[O-])cnc2C)ccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C14H14N4O6/c1-9-7-11(3-4-12(9)17(20)21)14(19)24-6-5-16-10(2)15-8-13(16)18(22)23/h3-4,7-8H,5-6H2,1-2H3

Standard InChI Key:  GTQUUKKQUUCHES-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   10.7998   -2.6209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4543   -2.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1929   -1.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3733   -1.3680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1344   -2.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8100   -3.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2367   -2.3742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8371   -1.8198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4166   -3.1713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5227   -3.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5328   -4.6550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2455   -5.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2557   -5.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9481   -4.6374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3609   -2.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5523   -6.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5621   -7.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2753   -7.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9802   -7.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9670   -6.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2893   -8.3223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0025   -8.7212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5873   -8.7406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6944   -7.4767    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  1  1  0
  1  6  1  0
  7  8  2  0
  7  9  1  0
  2  7  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 13  1  0
 21 22  2  0
 21 23  1  0
 18 21  1  0
 19 24  1  0
M  CHG  4   7   1   9  -1  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4100978

   2-(2-Methyl-5-nitroimidazol-1-yl)ethyl 3-methyl-4-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: 334.29

Molecular Weight (Monoisotopic): 334.0913

AlogP: 2.17

#Rotatable Bonds: 6

Polar Surface Area: 130.40

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.27

CX LogP: 2.49

CX LogD: 2.49

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.45

Np Likeness Score: -1.60

References

1. Salar U, Khan KM, Taha M, Ismail NH, Ali B, Qurat-Ul-Ain, Perveen S, Ghufran M, Wadood A..  (2017)  Biology-oriented drug synthesis (BIODS): In vitro β-glucuronidase inhibitory and in silico studies on 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl aryl carboxylate derivatives.,  125  [PMID:27886546] [10.1016/j.ejmech.2016.11.031]

Source

Source(1):

• Scientific Literature