2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-methylbenzoate

ID: ALA4104040

PubChem CID: 133716025

Max Phase: Preclinical

Molecular Formula: C14H15N3O4

Molecular Weight: 289.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)OCCn2c([N+](=O)[O-])cnc2C)cc1

Standard InChI:  InChI=1S/C14H15N3O4/c1-10-3-5-12(6-4-10)14(18)21-8-7-16-11(2)15-9-13(16)17(19)20/h3-6,9H,7-8H2,1-2H3

Standard InChI Key:  YZXYREWDNBUHAF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   13.3381  -18.6634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9926  -18.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7312  -17.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9115  -17.4106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6726  -18.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3482  -19.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7750  -18.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3754  -17.8623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9549  -19.2138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0609  -19.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0711  -20.6975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7838  -21.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7939  -21.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4864  -20.6800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8991  -18.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0906  -22.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1003  -23.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8136  -23.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5185  -23.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5052  -22.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8248  -24.3609    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
 18 21  1  0
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4104040

   ---

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: 289.29

Molecular Weight (Monoisotopic): 289.1063

AlogP: 2.27

#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: 2.55

CX LogD: 2.55

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.48

Np Likeness Score: -1.53

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