N,N'-Bis(3-nitrobenzylidene)cyclohexane-1,2-diamine

ID: ALA2230063

PubChem CID: 5046794

Max Phase: Preclinical

Molecular Formula: C20H20N4O4

Molecular Weight: 380.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cccc(/C=N/C2CCCCC2/N=C/c2cccc([N+](=O)[O-])c2)c1

Standard InChI:  InChI=1S/C20H20N4O4/c25-23(26)17-7-3-5-15(11-17)13-21-19-9-1-2-10-20(19)22-14-16-6-4-8-18(12-16)24(27)28/h3-8,11-14,19-20H,1-2,9-10H2/b21-13+,22-14+

Standard InChI Key:  BUVWLXJOISQWFF-JFMUQQRKSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   14.2236  -30.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6322  -29.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4535  -29.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8662  -30.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4535  -30.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6322  -30.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4023  -30.0661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2236  -28.6396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6322  -27.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2236  -27.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4023  -27.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9895  -26.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4023  -25.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2236  -25.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6322  -26.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1682  -26.5082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7555  -27.2173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7555  -25.7991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9895  -30.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1682  -30.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7555  -31.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9342  -31.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5215  -30.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9342  -30.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7555  -30.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5215  -32.2016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9342  -32.9066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7001  -32.2016    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  1  0
  5  6  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 16 17  2  0
 16 18  1  0
 12 16  1  0
  8  9  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 26 27  2  0
 26 28  1  0
 22 26  1  0
  7 19  2  0
M  CHG  4  16   1  18  -1  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2230063

   1-(3-nitrophenyl)-N-[2-[(3-nitrophenyl)methylideneamino]cyclohexyl]methanimine

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: 380.40

Molecular Weight (Monoisotopic): 380.1485

AlogP: 4.35

#Rotatable Bonds: 6

Polar Surface Area: 111.00

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.13

CX LogP: 4.97

CX LogD: 4.96

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -0.65

References

1. Aggarwal N, Kumar R, Dureja P, Rawat DS..  (2009)  Schiff bases as potential fungicides and nitrification inhibitors.,  57  (18): [PMID:19702271] [10.1021/jf902035w]

Source

Source(1):

• Scientific Literature