2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-chloro-4,5-difluorobenzoate

ID: ALA4084524

PubChem CID: 137647287

Max Phase: Preclinical

Molecular Formula: C13H10ClF2N3O4

Molecular Weight: 345.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncc([N+](=O)[O-])n1CCOC(=O)c1cc(F)c(F)cc1Cl

Standard InChI:  InChI=1S/C13H10ClF2N3O4/c1-7-17-6-12(19(21)22)18(7)2-3-23-13(20)8-4-10(15)11(16)5-9(8)14/h4-6H,2-3H2,1H3

Standard InChI Key:  UHNIYHZMQITKAW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.8207   -2.6952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793   -2.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179   -1.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3941   -1.4382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511   -2.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8308   -3.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2658   -2.4485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8704   -1.8899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4457   -3.2497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5477   -3.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5578   -4.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2746   -5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2848   -5.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9814   -4.7241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3735   -2.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5773   -6.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5871   -7.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3045   -7.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0135   -7.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0002   -6.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8801   -7.6167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.3157   -8.4215    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.7047   -5.9342    0.0000 Cl  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
 17 21  1  0
 18 22  1  0
 20 23  1  0
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4084524

   ---

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: 345.69

Molecular Weight (Monoisotopic): 345.0328

AlogP: 2.89

#Rotatable Bonds: 5

Polar Surface Area: 87.26

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.27

CX LogP: 2.93

CX LogD: 2.93

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.36

Np Likeness Score: -2.08

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]

2. Iraji A, Nouri A, Edraki N, Pirhadi S, Khoshneviszadeh M, Khoshneviszadeh M..  (2020)  One-pot synthesis of thioxo-tetrahydropyrimidine derivatives as potent β-glucuronidase inhibitor, biological evaluation, molecular docking and molecular dynamics studies.,  28  (7): [PMID:32098709] [10.1016/j.bmc.2020.115359]

Source

Source(1):

• Scientific Literature