Isoquinoline-5,8-dione

ID: ALA81679

Cas Number: 50-46-4

PubChem CID: 5766

Max Phase: Preclinical

Molecular Formula: C9H5NO2

Molecular Weight: 159.14

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Isoquinoline-5,8-dione | Isoquinoline-5,8-dione|5,8-ISOQUINOLINEDIONE|50-46-4|NSC-76882|NSC 76882|BRN 1525151|5-21-11-00263 (Beilstein Handbook Reference)|NSC76882|CF6NRA2TVB|isoquinoline-5,8-quinone|NCIOpen2_000894|CHEMBL81679|METHAQUALONEHYDROCHLORIDE|SCHEMBL6186385|DTXSID10198164|CUPFSRUOCULQSY-UHFFFAOYSA-N|AKOS006276227

Canonical SMILES:  O=C1C=CC(=O)c2cnccc21

Standard InChI:  InChI=1S/C9H5NO2/c11-8-1-2-9(12)7-5-10-4-3-6(7)8/h1-5H

Standard InChI Key:  CUPFSRUOCULQSY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 12 13  0  0  0  0  0  0  0  0999 V2000
    0.4792   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -1.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -0.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -2.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  5  2  0
  7 10  1  0
  8  3  2  0
  9  4  2  0
 10  1  2  0
 11  2  2  0
 12  7  2  0
 12 11  1  0
  4  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA81679

   5,8-Isoquinolinedione

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: 159.14

Molecular Weight (Monoisotopic): 159.0320

AlogP: 1.02

#Rotatable Bonds: ┄

Polar Surface Area: 47.03

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.18

CX LogP: 0.28

CX LogD: 0.28

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.57

Np Likeness Score: 0.29

References

1. Ryu CK, Jung SH, Lee JA, Kim HJ, Lee SH, Chung JH..  (1999)  6-arylamino-5,8-quinolinediones and 7-arylamino-5,8-isoquinolinediones as inhibitors of endothelium-dependent vasorelaxation.,  9  (17): [PMID:10498190] [10.1016/s0960-894x(99)00411-4]

2. Bernardo PH, Chai CL, Le Guen M, Smith GD, Waring P..  (2007)  Structure-activity delineation of quinones related to the biologically active Calothrixin B.,  17  (1): [PMID:17098429] [10.1016/j.bmcl.2006.09.090]

3. Alfadhli A, Mack A, Harper L, Berk S, Ritchie C, Barklis E..  (2016)  Analysis of quinolinequinone reactivity, cytotoxicity, and anti-HIV-1 properties.,  24  (21): [PMID:27663546] [10.1016/j.bmc.2016.09.028]

Source

Source(1):

• Scientific Literature