2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-chlorobenzoate

ID: ALA4088561

PubChem CID: 68779714

Max Phase: Preclinical

Molecular Formula: C13H12ClN3O4

Molecular Weight: 309.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncc([N+](=O)[O-])n1CCOC(=O)c1ccccc1Cl

Standard InChI:  InChI=1S/C13H12ClN3O4/c1-9-15-8-12(17(19)20)16(9)6-7-21-13(18)10-4-2-3-5-11(10)14/h2-5,8H,6-7H2,1H3

Standard InChI Key:  ZYBNESXCJCYEFK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   25.8931   -2.1133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5476   -1.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2862   -0.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4666   -0.8604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2277   -1.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9032   -2.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3300   -1.8665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9304   -1.3121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5099   -2.6636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6160   -3.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6261   -4.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3388   -4.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3489   -5.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0414   -4.1298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4541   -1.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6456   -5.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6554   -6.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3686   -6.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0735   -6.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0603   -5.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7606   -5.3357    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
 20 21  1  0
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4088561

   2-(2-Methyl-5-nitroimidazol-1-yl)ethyl 2-chlorobenzoate

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: 309.71

Molecular Weight (Monoisotopic): 309.0516

AlogP: 2.61

#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: 2.64

CX LogD: 2.64

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.48

Np Likeness Score: -1.87

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. Faghih-Mirzaei E, Sabouri S, Zeidabadinejad L, AbdolahRamazani S, Abaszadeh M, Khodadadi A, Shamsadinipour M, Jafari M, Pirhadi S..  (2019)  Metronidazole aryloxy, carboxy and azole derivatives: Synthesis, anti-tumor activity, QSAR, molecular docking and dynamics studies.,  27  (2): [PMID:30554970] [10.1016/j.bmc.2018.12.003]

Source

Source(1):

• Scientific Literature