8-chloro-2-hydroxypyrazino[1,2-a]indole-1,3(2H,4H)-dione

ID: ALA3806243

PubChem CID: 127050435

Max Phase: Preclinical

Molecular Formula: C11H7ClN2O3

Molecular Weight: 250.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Cn2c(cc3cc(Cl)ccc32)C(=O)N1O

Standard InChI:  InChI=1S/C11H7ClN2O3/c12-7-1-2-8-6(3-7)4-9-11(16)14(17)10(15)5-13(8)9/h1-4,17H,5H2

Standard InChI Key:  LPKKARULOOYORW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 19  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
   -4.7428   -1.1993    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
  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
M  END

Alternative Forms

1. Parent:

   

   ALA3806243

   ---

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: 250.64

Molecular Weight (Monoisotopic): 250.0145

AlogP: 1.67

#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: 1.36

CX LogD: 0.93

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.57

Np Likeness Score: -0.95

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