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

ID: ALA2252357

PubChem CID: 76329993

Max Phase: Preclinical

Molecular Formula: C22H26N6O2S2

Molecular Weight: 470.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=N/NC(=S)N2CCN(C(=S)N/N=C/c3ccc(OC)cc3)CC2)cc1

Standard InChI:  InChI=1S/C22H26N6O2S2/c1-29-19-7-3-17(4-8-19)15-23-25-21(31)27-11-13-28(14-12-27)22(32)26-24-16-18-5-9-20(30-2)10-6-18/h3-10,15-16H,11-14H2,1-2H3,(H,25,31)(H,26,32)/b23-15+,24-16+

Standard InChI Key:  XQZUHJIKMOJVBU-DFEHQXHXSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    7.8211  -13.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9957  -13.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5893  -13.8614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9957  -14.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211  -14.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2320  -13.8614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0533  -13.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4670  -14.5715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4650  -13.1479    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.2883  -14.5704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6959  -13.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5172  -13.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9263  -14.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7468  -14.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1552  -13.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7413  -13.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9221  -13.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7680  -13.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3563  -13.1479    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3543  -14.5715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5330  -14.5704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1254  -13.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3040  -13.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970  -13.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764  -13.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6660  -13.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0780  -14.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8973  -14.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8489  -13.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4403  -13.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9724  -13.8541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3791  -13.1453    0.0000 C   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
 26 29  1  0
 29 30  1  0
 15 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252357

   1-N,4-N-bis[(E)-(4-methoxyphenyl)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: 470.62

Molecular Weight (Monoisotopic): 470.1559

AlogP: 2.44

#Rotatable Bonds: 6

Polar Surface Area: 73.72

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.59

CX Basic pKa: 2.86

CX LogP: 3.57

CX LogD: 3.57

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.38

Np Likeness Score: -0.91

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