2-((2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)amino)-3-hydroxynaphthalene-1,4-dione

ID: ALA4546952

PubChem CID: 155552167

Max Phase: Preclinical

Molecular Formula: C18H13NO5

Molecular Weight: 323.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(O)=C(Nc2ccc3c(c2)OCCO3)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C18H13NO5/c20-16-11-3-1-2-4-12(11)17(21)18(22)15(16)19-10-5-6-13-14(9-10)24-8-7-23-13/h1-6,9,19,22H,7-8H2

Standard InChI Key:  KKCMDEWZFISKHC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   34.1061  -10.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1050  -11.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8200  -11.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8182  -10.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5338  -10.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5327  -11.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2459  -11.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9647  -11.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9659  -10.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2482  -10.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2482   -9.2923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2435  -12.6004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6816  -10.1244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6783  -11.7787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3942  -11.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1049  -11.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1045  -10.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3920  -10.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8230  -10.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8176  -11.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5247  -11.7891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.2419  -11.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2474  -10.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5356  -10.1406    0.0000 O   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 20  1  0
 19 17  1  0
 17 18  2  0
 18 15  1  0
 19 20  2  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4546952

   ---

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: 323.30

Molecular Weight (Monoisotopic): 323.0794

AlogP: 2.72

#Rotatable Bonds: 2

Polar Surface Area: 84.86

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.37

CX Basic pKa: ┄

CX LogP: 1.40

CX LogD: 0.33

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.88

Np Likeness Score: -0.36

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