2-Hydroxy-3-(4-(4-nitrophenyl)piperazin-1-yl)naphthalene-1,4-dione

ID: ALA4527976

PubChem CID: 155544523

Max Phase: Preclinical

Molecular Formula: C20H17N3O5

Molecular Weight: 379.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(O)=C(N2CCN(c3ccc([N+](=O)[O-])cc3)CC2)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C20H17N3O5/c24-18-15-3-1-2-4-16(15)19(25)20(26)17(18)22-11-9-21(10-12-22)13-5-7-14(8-6-13)23(27)28/h1-8,26H,9-12H2

Standard InChI Key:  ABQYVCSGTGHHMG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   26.5065  -26.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2215  -25.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2243  -25.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5060  -24.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7939  -25.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0889  -22.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0877  -23.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8025  -23.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8007  -22.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5161  -22.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5149  -23.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2277  -23.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9464  -23.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9476  -22.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2302  -22.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2302  -21.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2255  -24.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6630  -22.2028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6597  -23.8565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6522  -24.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3614  -25.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0793  -24.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0837  -23.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3700  -23.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9346  -26.3440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9319  -27.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6504  -25.9339    0.0000 O   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
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  9 12  2  0
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 13 18  2  0
 15 19  1  0
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 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
  3 26  1  0
 26 27  1  0
 26 28  2  0
M  CHG  2  26   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4527976

   ---

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: 379.37

Molecular Weight (Monoisotopic): 379.1168

AlogP: 2.57

#Rotatable Bonds: 3

Polar Surface Area: 103.99

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.84

CX Basic pKa: 0.29

CX LogP: 2.31

CX LogD: 1.65

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -0.72

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