N'1,N'4-bis(4-nitrobenzylidene)piperazine-1,4-bis(carbothiohydrazide)

ID: ALA2252359

PubChem CID: 76315479

Max Phase: Preclinical

Molecular Formula: C20H20N8O4S2

Molecular Weight: 500.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(/C=N/NC(=S)N2CCN(C(=S)N/N=C/c3ccc([N+](=O)[O-])cc3)CC2)cc1

Standard InChI:  InChI=1S/C20H20N8O4S2/c29-27(30)17-5-1-15(2-6-17)13-21-23-19(33)25-9-11-26(12-10-25)20(34)24-22-14-16-3-7-18(8-4-16)28(31)32/h1-8,13-14H,9-12H2,(H,23,33)(H,24,34)/b21-13+,22-14+

Standard InChI Key:  HGPFRHZWAWIGEO-JFMUQQRKSA-N

Molfile:  

     RDKit          2D

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   35.7955  -12.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9700  -12.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5637  -13.2671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9700  -13.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7955  -13.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   37.4413  -13.9772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4394  -12.5535    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   38.2626  -13.9761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.6703  -13.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4916  -13.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9006  -13.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7212  -13.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.5073  -13.9761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0997  -13.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2784  -13.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8714  -12.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0508  -12.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6404  -13.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0524  -13.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8716  -13.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8199  -13.2602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4112  -13.9679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4113  -12.5525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.9507  -13.2598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.3574  -12.5510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.3612  -13.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  3 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 29 30  2  0
 29 31  1  0
 26 29  1  0
 32 33  2  0
 32 34  1  0
 15 32  1  0
M  CHG  4  29   1  31  -1  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2252359

   1-N,4-N-bis[(E)-(4-nitrophenyl)methylideneamino]piperazine-1,4-dicarbothioamide

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: 500.57

Molecular Weight (Monoisotopic): 500.1049

AlogP: 2.24

#Rotatable Bonds: 6

Polar Surface Area: 141.54

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.59

CX Basic pKa: 2.06

CX LogP: 3.76

CX LogD: 3.76

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.26

Np Likeness Score: -1.15

References

1. Chandra R, Pandey OP, Sengupta SK..  (2005)  Organophosphorus derivatives containing piperazine dithiosemicarbazones as chemotherapeutants against fungal pathogens of sugarcane.,  53  (6): [PMID:15769154] [10.1021/jf040134m]

Source

Source(1):

• Scientific Literature