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

ID: ALA1093220

PubChem CID: 46886494

Max Phase: Preclinical

Molecular Formula: C18H18N2O4

Molecular Weight: 326.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H18N2O4/c1-10(21)11-5-7-13-14(9-11)20-18(19-13)12-6-8-15(22-2)17(24-4)16(12)23-3/h5-9H,1-4H3,(H,19,20)

Standard InChI Key:  MOBCYIQHLRMGIF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -4.9639  -18.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9651  -19.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503  -19.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521  -18.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5367  -18.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5364  -19.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7460  -19.8298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2576  -19.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7464  -18.4852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4359  -19.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0238  -19.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1995  -19.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135  -19.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2036  -18.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0265  -18.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0385  -19.1551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4522  -19.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4412  -17.7300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2662  -17.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061  -17.7237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0311  -17.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6785  -18.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6787  -17.5085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3988  -18.7461    0.0000 C   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
  1 22  1  0
 10 11  2  0
 22 23  2  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093220

   1-[2-(2,3,4-Trimethoxyphenyl)-1H-benzimidazol-5-yl]ethanone

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: 326.35

Molecular Weight (Monoisotopic): 326.1267

AlogP: 3.46

#Rotatable Bonds: 5

Polar Surface Area: 73.44

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.64

CX Basic pKa: 4.00

CX LogP: 2.37

CX LogD: 2.37

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: -0.48

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. Vitale G, Corona P, Loriga M, Carta A, Paglietti G, Giliberti G, Sanna G, Farci P, Marongiu ME, La Colla P..  (2012)  5-acetyl-2-arylbenzimidazoles as antiviral agents. Part 4.,  53  [PMID:22513121] [10.1016/j.ejmech.2012.03.038]

Source

Source(1):

• Scientific Literature