6-Amino-7-chloro-5,8-quinolinequinone

ID: ALA1098773

Cas Number: 18892-39-2

PubChem CID: 96583

Max Phase: Preclinical

Molecular Formula: C9H5ClN2O2

Molecular Weight: 208.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC1=C(Cl)C(=O)c2ncccc2C1=O

Standard InChI:  InChI=1S/C9H5ClN2O2/c10-5-6(11)8(13)4-2-1-3-12-7(4)9(5)14/h1-3H,11H2

Standard InChI Key:  KWGIFJNXSKZGKI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
    7.0588    2.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0588    1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7696    1.3315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7696    2.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4850    2.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4861    1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1975    1.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9123    1.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9112    2.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1953    2.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1931    3.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1974    0.5116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6219    2.9797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6230    1.3333    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5  6  2  0
 10 11  2  0
  7 12  2  0
  1  2  1  0
  9 13  1  0
  1  4  2  0
  8 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1098773

   6-Amino-7-chloro-5,8-dioxoquinoline

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: 208.60

Molecular Weight (Monoisotopic): 208.0040

AlogP: 0.87

#Rotatable Bonds: ┄

Polar Surface Area: 73.05

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.10

CX LogD: -0.10

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.69

Np Likeness Score: 0.31

References

1. Mulchin BJ, Newton CG, Baty JW, Grasso CH, Martin WJ, Walton MC, Dangerfield EM, Plunkett CH, Berridge MV, Harper JL, Timmer MS, Stocker BL..  (2010)  The anti-cancer, anti-inflammatory and tuberculostatic activities of a series of 6,7-substituted-5,8-quinolinequinones.,  18  (9): [PMID:20363637] [10.1016/j.bmc.2010.03.021]

2.  (2013)  Chemical agents for the prevention of inhibition or tumor metastasis, 

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]

4. Hu Y,Wang L,Han X,Zhou Y,Zhang T,Wang L,Hong T,Zhang W,Guo XX,Sun J,Qi Y,Yu J,Liu H,Wu F.  (2019)  Discovery of a Bioactive Inhibitor with a New Scaffold for Cystathionine γ-Lyase.,  62  (3): [PMID:30562026] [10.1021/acs.jmedchem.8b01720]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data