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

ID: ALA4452960

PubChem CID: 155522616

Max Phase: Preclinical

Molecular Formula: C16H10ClNO3

Molecular Weight: 299.71

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(O)=C(Nc2ccccc2Cl)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C16H10ClNO3/c17-11-7-3-4-8-12(11)18-13-14(19)9-5-1-2-6-10(9)15(20)16(13)21/h1-8,18,21H

Standard InChI Key:  QSUMXMNYTTXIMB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    2.9485  -10.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9473  -11.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621  -11.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6603  -10.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3756  -10.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3744  -11.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0873  -11.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8060  -11.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8072  -10.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0897  -10.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0898   -9.1929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0850  -12.4998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5227  -10.0247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5193  -11.6784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2349  -11.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9454  -11.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6604  -11.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6632  -10.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9449  -10.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2328  -10.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9405  -12.5110    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
 16 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4452960

   ---

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: 299.71

Molecular Weight (Monoisotopic): 299.0349

AlogP: 3.60

#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: 6.19

CX Basic pKa: ┄

CX LogP: 2.50

CX LogD: 1.27

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.89

Np Likeness Score: -0.50

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