2-Hydroxy-8-methoxypyrazino[1,2-a]indole-1,3(2H,4H)-dione

ID: ALA3805012

PubChem CID: 127051976

Max Phase: Preclinical

Molecular Formula: C12H10N2O4

Molecular Weight: 246.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)cc1n2CC(=O)N(O)C1=O

Standard InChI:  InChI=1S/C12H10N2O4/c1-18-8-2-3-9-7(4-8)5-10-12(16)14(17)11(15)6-13(9)10/h2-5,17H,6H2,1H3

Standard InChI Key:  HZMZWEIVNVEQGX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 20  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
   -4.9998   -1.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9984   -2.5577    0.0000 C   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
  1 17  1  0
 17 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3805012

   ---

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: 246.22

Molecular Weight (Monoisotopic): 246.0641

AlogP: 1.02

#Rotatable Bonds: 1

Polar Surface Area: 71.77

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.17

CX Basic pKa: ┄

CX LogP: 0.60

CX LogD: 0.17

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.60

Np Likeness Score: -0.51

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]

Source

Source(1):

• Scientific Literature