2-((2,3-Dichlorophenyl)amino)-3-hydroxynaphthalene-1,4-dione

ID: ALA4540838

PubChem CID: 155550675

Max Phase: Preclinical

Molecular Formula: C16H9Cl2NO3

Molecular Weight: 334.16

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(O)=C(Nc2cccc(Cl)c2Cl)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C16H9Cl2NO3/c17-10-6-3-7-11(12(10)18)19-13-14(20)8-4-1-2-5-9(8)15(21)16(13)22/h1-7,19,22H

Standard InChI Key:  PNWQTTYCANNOIS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   26.3770  -16.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3758  -17.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0906  -18.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0888  -16.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8042  -16.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8030  -17.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5159  -18.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2346  -17.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2358  -16.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5183  -16.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5183  -15.6512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5137  -18.9581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9512  -16.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9479  -18.1367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6635  -17.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3740  -18.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0890  -17.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0918  -16.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3735  -16.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6613  -16.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8021  -18.1494    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   31.3691  -18.9693    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  7 12  2  0
  9 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 17 21  1  0
 16 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4540838

   ---

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: 334.16

Molecular Weight (Monoisotopic): 332.9959

AlogP: 4.25

#Rotatable Bonds: 2

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.84

CX Basic pKa: ┄

CX LogP: 3.10

CX LogD: 1.53

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.86

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