(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N-benzyl-2-cyanopenta-2,4-dienamide

ID: ALA4540338

PubChem CID: 11559017

Max Phase: Preclinical

Molecular Formula: C20H16N2O3

Molecular Weight: 332.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#C/C(=C\C=C\c1ccc2c(c1)OCO2)C(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C20H16N2O3/c21-12-17(20(23)22-13-16-5-2-1-3-6-16)8-4-7-15-9-10-18-19(11-15)25-14-24-18/h1-11H,13-14H2,(H,22,23)/b7-4+,17-8+

Standard InChI Key:  UURWETMCUDXPLA-AQHRCUNFSA-N

Molfile:  

 
     RDKit          2D

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   32.6500  -13.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6472  -13.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9386  -12.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2323  -13.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2290  -13.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4514  -12.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9741  -13.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4568  -14.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3533  -12.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0626  -13.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7687  -12.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4780  -13.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1842  -12.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1811  -11.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8934  -13.1586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4835  -13.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4866  -14.7945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5996  -12.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3088  -13.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3093  -13.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0177  -14.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7248  -13.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7191  -13.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0101  -12.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  3 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 17 18  3  0
 13 17  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4540338

   (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-benzyl-2-cyanopenta-2,4-dienamide

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: 332.36

Molecular Weight (Monoisotopic): 332.1161

AlogP: 3.19

#Rotatable Bonds: 5

Polar Surface Area: 71.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.04

CX Basic pKa: ┄

CX LogP: 3.24

CX LogD: 3.24

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.52

Np Likeness Score: -0.49

References

1. Chavarria D, Fernandes C, Silva V, Silva C, Gil-Martins E, Soares P, Silva T, Silva R, Remião F, Oliveira PJ, Borges F..  (2020)  Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies.,  185  [PMID:31711793] [10.1016/j.ejmech.2019.111770]

Source

Source(1):

• Scientific Literature