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

ID: ALA4092265

Cas Number: 1252131-29-5

PubChem CID: 51076459

Max Phase: Preclinical

Molecular Formula: C15H14N4O4

Molecular Weight: 314.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncc([N+](=O)[O-])n1CCOC(=O)c1cc2ccccc2[nH]1

Standard InChI:  InChI=1S/C15H14N4O4/c1-10-16-9-14(19(21)22)18(10)6-7-23-15(20)13-8-11-4-2-3-5-12(11)17-13/h2-5,8-9,17H,6-7H2,1H3

Standard InChI Key:  XINBFVWEHZUCKZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   17.7955   -2.1091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4541   -1.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1927   -0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3689   -0.8521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1301   -1.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8056   -2.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2406   -1.8624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8452   -1.3039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4205   -2.6636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5225   -3.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5326   -4.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2494   -4.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2596   -5.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9561   -4.1380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3524   -1.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6013   -5.8669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9316   -5.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6889   -6.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8696   -6.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4680   -7.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8888   -8.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7111   -8.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1048   -7.3350    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  1  0
 16 19  1  0
 18 17  1  0
 17 13  2  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4092265

   2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 1H-indole-2-carboxylate

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: 314.30

Molecular Weight (Monoisotopic): 314.1015

AlogP: 2.44

#Rotatable Bonds: 5

Polar Surface Area: 103.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.25

CX Basic pKa: 3.27

CX LogP: 2.05

CX LogD: 2.05

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.44

Np Likeness Score: -1.56

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