IMPPAT Phytochemical information: 
6-Hydroxyquinoline

6-Hydroxyquinoline
Summary

SMILES: Oc1ccc2c(c1)cccn2
InChI: InChI=1S/C9H7NO/c11-8-3-4-9-7(6-8)2-1-5-10-9/h1-6,11H
InChIKey: OVYWMEWYEJLIER-UHFFFAOYSA-N
DeepSMILES: Occcccc6)cccn6
Scaffold Graph/Node/Bond level: c1ccc2ncccc2c1
Scaffold Graph/Node level: C1CCC2NCCCC2C1
Scaffold Graph level: C1CCC2CCCCC2C1
Functional groups: cO; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Hydroxyquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids|Anthranilic acid alkaloids
NP Classifier Class: Quinoline alkaloids
Synonymous chemical names:
6-hydroxyquinoline
External chemical identifiers:
CID:CID_11374; ChEMBL:CHEMBL1908053; ChEBI:CHEBI:48994; ZINC:ZINC000000331725; FDASRS:95RU6I7UXL; SureChEMBL:SCHEMBL112289; MolPort-000-140-082
Chemical structure download


6-Hydroxyquinoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 145.16
Log P RDKit 1.94
Topological polar surface area (Å2) RDKit 33.12
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 11
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


6-Hydroxyquinoline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.614103


6-Hydroxyquinoline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.91
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


6-Hydroxyquinoline
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000341045UGT2B15700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.