(E/Z)-2-(N-isobutylbenzimidazol-2-yl)-3-(4-nitrophenyl)acrylonitrile

ID: ALA4875812

PubChem CID: 164626531

Max Phase: Preclinical

Molecular Formula: C20H18N4O2

Molecular Weight: 346.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)Cn1c(C(C#N)=Cc2ccc([N+](=O)[O-])cc2)nc2ccccc21

Standard InChI:  InChI=1S/C20H18N4O2/c1-14(2)13-23-19-6-4-3-5-18(19)22-20(23)16(12-21)11-15-7-9-17(10-8-15)24(25)26/h3-11,14H,13H2,1-2H3

Standard InChI Key:  DBMHSSLAAXRUPQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    7.5484   -3.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2581   -3.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2553   -2.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5466   -1.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8404   -3.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8416   -2.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0654   -2.1309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5844   -2.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0634   -3.4520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7672   -2.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3597   -2.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9494   -1.3709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3576   -3.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5404   -3.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1360   -2.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196   -2.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091   -3.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3211   -4.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1362   -4.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8098   -4.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3557   -4.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1020   -5.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1553   -4.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0931   -3.4927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6854   -2.7848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -4.2013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
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  9  5  1  0
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 10 13  2  3
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 17 18  1  0
 18 19  2  0
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  9 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 24 25  1  0
 24 26  2  0
 17 24  1  0
M  CHG  2  24   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4875812

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 346.39

Molecular Weight (Monoisotopic): 346.1430

AlogP: 4.66

#Rotatable Bonds: 5

Polar Surface Area: 84.75

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.23

CX LogP: 5.10

CX LogD: 5.10

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.38

Np Likeness Score: -1.61

References

1. Perin N, Hok L, Beč A, Persoons L, Vanstreels E, Daelemans D, Vianello R, Hranjec M..  (2021)  N-substituted benzimidazole acrylonitriles as in vitro tubulin polymerization inhibitors: Synthesis, biological activity and computational analysis.,  211  [PMID:33248847] [10.1016/j.ejmech.2020.113003]

Source

Source(1):

• Scientific Literature