bis(diethoxyphosphoryl)N1,N4-bis[(2-chlorophenyl)methyleneamino]piperazine-1,4-dicarboximidothioate

ID: ALA2252243

PubChem CID: 76311928

Max Phase: Preclinical

Molecular Formula: C28H38Cl2N6O6P2S2

Molecular Weight: 751.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(OCC)S/C(=N/N=C/c1ccccc1Cl)N1CCN(/C(=N\N=C\c2ccccc2Cl)SP(=O)(OCC)OCC)CC1

Standard InChI:  InChI=1S/C28H38Cl2N6O6P2S2/c1-5-39-43(37,40-6-2)45-27(33-31-21-23-13-9-11-15-25(23)29)35-17-19-36(20-18-35)28(46-44(38,41-7-3)42-8-4)34-32-22-24-14-10-12-16-26(24)30/h9-16,21-22H,5-8,17-20H2,1-4H3/b31-21+,32-22+,33-27+,34-28+

Standard InChI Key:  YQMRUXXIADYQHR-GNGADACMSA-N

Molfile:  

     RDKit          2D

 46 48  0  0  0  0  0  0  0  0999 V2000
   36.0431  -21.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2240  -21.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8004  -22.5017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2000  -23.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0191  -23.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4386  -22.5295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2578  -22.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6814  -21.8403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2818  -21.1235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7054  -20.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3058  -19.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4867  -19.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0912  -18.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5107  -18.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3298  -18.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7295  -19.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9812  -22.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5857  -21.7710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6098  -20.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0293  -19.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6338  -18.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0533  -18.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8724  -18.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2721  -18.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8484  -19.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5617  -23.1909    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.7426  -23.1770    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   34.0052  -21.0680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6574  -23.2602    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   38.4765  -23.2741    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   38.8731  -23.9886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8970  -22.5734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2912  -23.2734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3460  -22.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3220  -23.8777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9241  -23.1703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5214  -22.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7042  -22.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5050  -23.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0845  -24.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6992  -22.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5164  -22.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6902  -24.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0867  -24.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8167  -18.9163    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   38.5466  -19.0134    0.0000 Cl  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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  3 17  1  0
 17 18  2  0
 18 28  1  0
 28 19  2  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
 17 26  1  0
 26 27  1  0
  7 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 30 33  1  0
 27 34  2  0
 27 35  1  0
 27 36  1  0
 36 37  1  0
 37 38  1  0
 35 39  1  0
 39 40  1  0
 33 41  1  0
 41 42  1  0
 31 43  1  0
 43 44  1  0
 21 45  1  0
 16 46  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252243

   bis(diethoxyphosphoryl) (1E,4E)-1-N,4-N-bis[(E)-(2-chlorophenyl)methylideneamino]piperazine-1,4-dicarboximidothioate

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: 751.64

Molecular Weight (Monoisotopic): 750.1147

AlogP: 8.52

#Rotatable Bonds: 14

Polar Surface Area: 126.98

Molecular Species: NEUTRAL

HBA: 12

HBD: ┄

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 1.09

CX LogP: 6.97

CX LogD: 6.97

Aromatic Rings: 2

Heavy Atoms: 46

QED Weighted: 0.08

Np Likeness Score: -0.55

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