IMPPAT Phytochemical information: 
2,8-Dihydroxy-4-quinolinecarboxylic acid

2,8-Dihydroxy-4-quinolinecarboxylic acid
Summary

SMILES: OC(=O)c1cc(=O)[nH]c2c1cccc2O
InChI: InChI=1S/C10H7NO4/c12-7-3-1-2-5-6(10(14)15)4-8(13)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)
InChIKey: DVEVPRIOUKVFAM-UHFFFAOYSA-N
DeepSMILES: OC=O)ccc=O)[nH]cc6cccc6O
Scaffold Graph/Node/Bond level: O=c1ccc2ccccc2[nH]1
Scaffold Graph/Node level: OC1CCC2CCCCC2N1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: cC(=O)O; c=O; c[nH]c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Quinoline carboxylic acids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids|Anthranilic acid alkaloids
NP Classifier Class: Quinoline alkaloids
Synonymous chemical names:
zeanic acid
External chemical identifiers:
CID:CID_13988328; ChEBI:CHEBI:173574; ZINC:ZINC000015116104; MolPort-028-750-745
Chemical structure download


2,8-Dihydroxy-4-quinolinecarboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 205.17
Log P RDKit 0.93
Topological polar surface area (Å2) RDKit 90.39
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 15
Number of heteroatoms RDKit 5
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 10
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 1
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


2,8-Dihydroxy-4-quinolinecarboxylic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.65


2,8-Dihydroxy-4-quinolinecarboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.40
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No