5-Nitro-2-(4-trimethoxyphenyl)-1H-benzimidazole

ID: ALA1092984

PubChem CID: 46845159

Max Phase: Preclinical

Molecular Formula: C16H15N3O5

Molecular Weight: 329.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2nc3cc([N+](=O)[O-])ccc3[nH]2)c(OC)c1OC

Standard InChI:  InChI=1S/C16H15N3O5/c1-22-13-7-5-10(14(23-2)15(13)24-3)16-17-11-6-4-9(19(20)21)8-12(11)18-16/h4-8H,1-3H3,(H,17,18)

Standard InChI Key:  IRXXSDFWKUMWQA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    4.9819  -15.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807  -15.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6956  -16.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938  -14.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4091  -15.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4094  -15.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1999  -16.2423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6882  -15.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1994  -14.8977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5099  -15.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9221  -16.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7463  -16.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1594  -15.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7422  -14.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9193  -14.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9844  -15.5676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3981  -16.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5046  -14.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6796  -14.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1519  -14.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9769  -14.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2666  -14.7462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5522  -15.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2664  -13.9212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
  5  4  2  0
 13 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 15 18  1  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 14 20  1  0
  4  1  1  0
 20 21  1  0
  5  6  1  0
 10 11  2  0
 22 23  2  0
 22 24  1  0
  1 22  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1092984

   5-Nitro-2-(2,3,4-trimethoxyphenyl)-1H-benzimidazole

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: 329.31

Molecular Weight (Monoisotopic): 329.1012

AlogP: 3.16

#Rotatable Bonds: 5

Polar Surface Area: 99.51

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.05

CX Basic pKa: 3.00

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.57

Np Likeness Score: -0.84

References

1. Tonelli M, Simone M, Tasso B, Novelli F, Boido V, Sparatore F, Paglietti G, Pricl S, Giliberti G, Blois S, Ibba C, Sanna G, Loddo R, La Colla P..  (2010)  Antiviral activity of benzimidazole derivatives. II. Antiviral activity of 2-phenylbenzimidazole derivatives.,  18  (8): [PMID:20359898] [10.1016/j.bmc.2010.02.037]

2. Navarrete-Vázquez G, Hidalgo-Figueroa S, Torres-Piedra M, Vergara-Galicia J, Rivera-Leyva JC, Estrada-Soto S, Estrada-Soto S, León-Rivera I, Aguilar-Guardarrama B, Rios-Gómez Y, Villalobos-Molina R, Ibarra-Barajas M..  (2010)  Synthesis, vasorelaxant activity and antihypertensive effect of benzo[d]imidazole derivatives.,  18  (11): [PMID:20451399] [10.1016/j.bmc.2010.04.027]

Source

Source(1):

• Scientific Literature