2-(4-(2,3-Dichlorophenyl)piperazin-1-yl)-3-hydroxynaphthalene-1,4-dione

ID: ALA4586212

PubChem CID: 155567039

Max Phase: Preclinical

Molecular Formula: C20H16Cl2N2O3

Molecular Weight: 403.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(O)=C(N2CCN(c3cccc(Cl)c3Cl)CC2)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C20H16Cl2N2O3/c21-14-6-3-7-15(16(14)22)23-8-10-24(11-9-23)17-18(25)12-4-1-2-5-13(12)19(26)20(17)27/h1-7,27H,8-11H2

Standard InChI Key:  NZGZDODHKDOVOY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   17.1842  -26.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8947  -26.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6098  -26.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6125  -25.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8942  -25.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1821  -25.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4771  -22.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4760  -23.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1907  -24.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1889  -22.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9042  -22.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9031  -23.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6160  -24.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3346  -23.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3358  -22.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6183  -22.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6183  -21.6837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6137  -24.9906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0512  -22.5155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0479  -24.1691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0404  -24.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7496  -25.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4677  -24.9982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4719  -24.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7582  -23.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8936  -24.1768    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.3276  -25.0047    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
 11 10  2  0
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 11 12  1  0
 11 16  1  0
 12 13  1  0
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 15 16  1  0
 16 17  2  0
 13 18  2  0
 15 19  1  0
 14 20  1  0
 20 21  1  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23  6  1  0
  5 26  1  0
  4 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4586212

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 403.27

Molecular Weight (Monoisotopic): 402.0538

AlogP: 3.96

#Rotatable Bonds: 2

Polar Surface Area: 60.85

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.46

CX Basic pKa: ┄

CX LogP: 3.58

CX LogD: 2.60

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -0.54

References

1. Calil FA, David JS, Chiappetta ERC, Fumagalli F, Mello RB, Leite FHA, Castilho MS, Emery FS, Nonato MC..  (2019)  Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.,  167  [PMID:30776695] [10.1016/j.ejmech.2019.02.018]

Source

Source(1):

• Scientific Literature