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

Names and Identifiers

Canonical SMILES: O=C1C(O)=C(Nc2ccc(Cl)cc2)C(=O)c2ccccc21

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

Standard InChI Key: CFMCHTLGLDUAFH-UHFFFAOYSA-N

Molfile:

 
     RDKit          2D

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   19.3906  -18.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3889  -16.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1043  -16.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1031  -17.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8160  -18.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5347  -17.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5359  -16.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8183  -16.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8184  -15.6511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8137  -18.9580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2513  -16.4828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2480  -18.1365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9635  -17.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6740  -18.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3891  -17.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3919  -16.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6735  -16.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9614  -16.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1069  -16.4972    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
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  7 12  2  0
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 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
M  END

Alternative Forms

Parent:

ALA4560384
2-(4-Chloroanilino)-3-hydroxynaphthoquinone

Associated Targets(Human)

DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)

Discover Target: DHODH

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Dihydroorotate dehydrogenase (quinone), mitochondrial (72 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

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: 6.21	CX Basic pKa: ┄	CX LogP: 2.50	CX LogD: 1.28
Aromatic Rings: 2	Heavy Atoms: 21	QED Weighted: 0.89	Np Likeness Score: -0.43

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