2-Hydroxypyrazino[1,2-a]indole-1,3(2H,4H)-dione

ID: ALA3805084

PubChem CID: 71656048

Max Phase: Preclinical

Molecular Formula: C11H8N2O3

Molecular Weight: 216.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Cn2c(cc3ccccc32)C(=O)N1O

Standard InChI:  InChI=1S/C11H8N2O3/c14-10-6-12-8-4-2-1-3-7(8)5-9(12)11(15)13(10)16/h1-5,16H,6H2

Standard InChI Key:  HNWXLPRAYJKYNF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 18  0  0  0  0  0  0  0  0999 V2000
   -3.7006   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7006    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274    0.8244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372   -0.6045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694   -2.5190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7737   -1.2093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7737    1.4291    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
  6  9  1  0
  8  7  2  0
  7  5  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  1  0
 11 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3805084

   2-hydroxy-4H-pyrazino[1,2-a]indole-1,3-dione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 216.20

Molecular Weight (Monoisotopic): 216.0535

AlogP: 1.01

#Rotatable Bonds: ┄

Polar Surface Area: 62.54

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.17

CX Basic pKa: ┄

CX LogP: 0.75

CX LogD: 0.32

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.53

Np Likeness Score: -0.53

References

1. Zoidis G, Giannakopoulou E, Stevaert A, Frakolaki E, Myrianthopoulos V, Fytas G, Mavromara P, Mikros E, Bartenschlager R, Vassilaki N, Naesens L.  (2016)  Novel indoleflutimide heterocycles with activity against influenza PA endonuclease and hepatitis C virus,  7  (3): [10.1039/C5MD00439J]

2. Giannakopoulou E, Pardali V, Frakolaki E, Siozos V, Myrianthopoulos V, Mikros E, Taylor MC, Kelly JM, Vassilaki N, Zoidis G..  (2019)  Scaffold hybridization strategy towards potent hydroxamate-based inhibitors of Flaviviridae viruses and Trypanosoma species.,  10  (6): [PMID:31303998] [10.1039/C9MD00200F]

Source

Source(1):

• Scientific Literature