(E)-N'-((E)-3-(2-nitrophenyl)allylidene)-2,3-dihydrobenzo[b][1,4]dioxine-5-carbohydrazide

ID: ALA5274125

Max Phase: Preclinical

Molecular Formula: C18H15N3O5

Molecular Weight: 353.33

Names and Identifiers

Canonical SMILES:  O=C(N/N=C/C=C/c1ccccc1[N+](=O)[O-])c1cccc2c1OCCO2

Standard InChI:  InChI=1S/C18H15N3O5/c22-18(14-7-3-9-16-17(14)26-12-11-25-16)20-19-10-4-6-13-5-1-2-8-15(13)21(23)24/h1-10H,11-12H2,(H,20,22)/b6-4+,19-10+

Standard InChI Key:  CWRCLHRBVIKIPS-CMHRUIPMSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -3.9264   -0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -1.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2120   -1.4419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4976   -1.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4976   -0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2120    0.2081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684   -1.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7799   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4993    1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708    1.4434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3565    1.0310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2147    1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    1.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2165   -0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -0.2095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -1.0342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719    0.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  1  0
  5  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  4 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 18 23  1  0
 24 23  1  0
 24 25  2  0
 24 26  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5274125

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 353.33

Molecular Weight (Monoisotopic): 353.1012

AlogP: 2.80

#Rotatable Bonds: 5

Polar Surface Area: 103.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.67

CX Basic pKa: 1.38

CX LogP: 2.71

CX LogD: 2.71

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: -1.51

References

1. Bolchi C, Bavo F, Appiani R, Roda G, Pallavicini M..  (2020)  1,4-Benzodioxane, an evergreen, versatile scaffold in medicinal chemistry: A review of its recent applications in drug design.,  200  [PMID:32502862] [10.1016/j.ejmech.2020.112419]

Source

Source(1):

• Scientific Literature