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

ID: ALA4474026

PubChem CID: 155536717

Max Phase: Preclinical

Molecular Formula: C20H17ClN2O3

Molecular Weight: 368.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(O)=C(N2CCN(c3ccc(Cl)cc3)CC2)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C20H17ClN2O3/c21-13-5-7-14(8-6-13)22-9-11-23(12-10-22)17-18(24)15-3-1-2-4-16(15)19(25)20(17)26/h1-8,26H,9-12H2

Standard InChI Key:  YVSSKYRZGDZBSW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.6227  -26.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3376  -26.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9196  -24.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6331  -22.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6319  -23.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0632  -23.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0644  -22.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3471  -21.7425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3424  -25.0487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7797  -22.5740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7764  -24.2274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7689  -25.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4780  -25.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1958  -25.0564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2002  -24.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4866  -23.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0506  -26.7146    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474026

   ---

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: 368.82

Molecular Weight (Monoisotopic): 368.0928

AlogP: 3.31

#Rotatable Bonds: 2

Polar Surface Area: 60.85

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.03

CX Basic pKa: 2.71

CX LogP: 2.98

CX LogD: 2.46

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.88

Np Likeness Score: -0.60

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