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Showing NP-Card for 8 hydroxyquinoline (NP0287895)

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Record Information
Version2.0
Created at2022-09-09 17:22:34 UTC
Updated at2022-09-09 17:22:34 UTC
NP-MRD IDNP0287895
Secondary Accession NumbersNone
Natural Product Identification
Common Name8 hydroxyquinoline
DescriptionOxyquinoline, also known as 8-quinolinol or 8-OQ, belongs to the class of organic compounds known as 8-hydroxyquinolines. 8-Hydroxyquinolines are compounds containing a quinoline moiety, which carries a hydroxy group at the 8-position. Quinoline consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene. Oxyquinoline is a heterocyclic phenol and derivative of quinoline with antiseptic, disinfectant, and pesticide properties. In the urine, 60% of the dose is excreted as glucuronide conjugates and 23% of the dose as sulfate conjugates. In the bile, 9% of the total dose is found as glucuronide conjugates. Oxyquinoline is a strong basic compound (based on its pKa). Oxyquinoline exists in all living organisms, ranging from bacteria to humans. 8 hydroxyquinoline is found in Allium stipitatum and Cortinarius subtortus. 8 hydroxyquinoline was first documented in 1996 (PMID: 8877786). It is used as a stabilizer for hydrogen peroxide, where it is sometimes added in cosmetic products (PMID: 24206710) (PMID: 24445658) (PMID: 26067700).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0287895 (8 hydroxyquinoline)


  Mrv1652310081717422D          

 11 12  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
Download

3D MOL for NP0287895 (8 hydroxyquinoline)

     RDKit          3D

 18 19  0  0  0  0  0  0  0  0999 V2000
    1.7484    2.3261   -0.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855    0.9905   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3719    0.0015    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536   -1.3372    0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7276   -1.6972    0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2552   -0.7138    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -1.0472    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688   -0.0661   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    1.2697   -0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9255    1.5832   -0.0813 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0486    0.6342   -0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0246    3.0225   -0.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4111    0.2899    0.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8134   -2.1188    0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4265   -2.7482    0.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8206   -2.1073    0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6158   -0.3445   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9925    2.0627   -0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
 11  2  1  0
  7  6  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  9 18  1  0
  8 17  1  0
  7 16  1  0
M  END
Download

3D SDF for NP0287895 (8 hydroxyquinoline)


  Mrv1652310081717422D          

 11 12  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287895

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC2=C1N=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H

> <INCHI_KEY>
MCJGNVYPOGVAJF-UHFFFAOYSA-N

> <FORMULA>
C9H7NO

> <MOLECULAR_WEIGHT>
145.158

> <EXACT_MASS>
145.052763851

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.866872454340452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
quinolin-8-ol

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.8273351496666665

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.357697226795183

> <JCHEM_PKA_STRONGEST_BASIC>
4.827847757000724

> <JCHEM_POLAR_SURFACE_AREA>
33.120000000000005

> <JCHEM_REFRACTIVITY>
41.9602

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8 hydroxyquinoline

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0287895 (8 hydroxyquinoline)

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PDB for NP0287895 (8 hydroxyquinoline)
HEADER    PROTEIN                                 08-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-17         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    7                                                       
CONECT    5    1    8                                                       
CONECT    6    2   10                                                       
CONECT    7    3    4    9                                                  
CONECT    8    5    9   11                                                  
CONECT    9    7    8   10                                                  
CONECT   10    6    9                                                       
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0287895 (8 hydroxyquinoline)
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SMILES for NP0287895 (8 hydroxyquinoline)
OC1=CC=CC2=C1N=CC=C2
Download
INCHI for NP0287895 (8 hydroxyquinoline)
InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
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View in JSmol
Synonyms
ValueSource
1-Azanaphthalene-8-olChEBI
8-ChinolinolChEBI
8-Hydroxy-chinolinChEBI
8-HydroxyquinolineChEBI
8-OQChEBI
8-QuinolChEBI
8-QuinolinolChEBI
8 QuinolinolMeSH
8 Hydroxyquinoline sulfateMeSH
OxineMeSH
Oxyquinoline potassium sulfate (2:1)MeSH
BioquinMeSH
Sulfate, oxyquinolineMeSH
KhinozolMeSH
8-OxyquinolineMeSH
SuperolMeSH
ChinosolMeSH
8-Hydroxyquinoline sulfateMeSH
OxyquinolMeSH
8 HydroxyquinolineMeSH
QuinosolMeSH
LeiodermMeSH
Oxyquinoline sulfateMeSH
Sulfate, 8-hydroxyquinolineMeSH
8 OxyquinolineMeSH
OxyquinolineChEBI
Tendem brand OF oxyquinoline sulfateMeSH
Chinosol brand OF oxyquinoline potassium sulfate (2:1)MeSH
Riemser brand OF oxyquinoline sulfateMeSH
Chemical FormulaC9H7NO
Average Mass145.1580 Da
Monoisotopic Mass145.05276 Da
IUPAC Namequinolin-8-ol
Traditional Name8 hydroxyquinoline
CAS Registry NumberNot Available
SMILES
OC1=CC=CC2=C1N=CC=C2
InChI Identifier
InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
InChI KeyMCJGNVYPOGVAJF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium stipitatumLOTUS Database
Cortinarius subtortusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-hydroxyquinolines. 8-Hydroxyquinolines are compounds containing a quinoline moiety, which carries a hydroxy group at the 8-position. Quinoline consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassQuinolines and derivatives  
Sub Class8-hydroxyquinolines  
Direct Parent8-hydroxyquinolines  
Alternative Parents
Substituents
  • 8-hydroxyquinoline
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Pyridine
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.91ALOGPS
logP1.83ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)9.36ChemAxon
pKa (Strongest Basic)4.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.96 m³·mol⁻¹ChemAxon
Polarizability14.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0165772  
DrugBank IDDB11145  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC19434  
BioCyc ID8-HYDROXYQUINOLINE  
BiGG IDNot Available
Wikipedia Link8-Hydroxyquinoline  
METLIN IDNot Available
PubChem Compound1923  
PDB IDNot Available
ChEBI ID48981  
Good Scents IDNot Available
References
General References
  1. Feist B, Mikula B: Preconcentration of some metal ions with lanthanum-8-hydroxyquinoline co-precipitation system. Food Chem. 2014 Mar 15;147:225-9. doi: 10.1016/j.foodchem.2013.09.149. Epub 2013  Oct 8. [PubMed:24206710  ] 
  2. Brooks AC, Basore K, Bernhard S: Organocatalytic photoreduction of Zn(II) to zinc metal. Chem Commun (Camb). 2014 May 25;50(40):5196-9. doi: 10.1039/c3cc47633b. Epub 2014  Jan 21. [PubMed:24445658  ] 
  3. Yan S, Chen L, Dou X, Qi M, Du Q, He Q, Nan M, Chang Z, Nan P: Toxicity of 8-Hydroxyquinoline in Cryprinus carpio Using the Acute Toxicity Test, Hepatase Activity Analysis and the Comet Assay. Bull Environ Contam Toxicol. 2015 Aug;95(2):171-6. doi:  10.1007/s00128-015-1566-9. Epub 2015 Jun 12. [PubMed:26067700  ] 
  4. Oubidar M, Marie C, Mossiat C, Bralet J: Effects of increasing intracellular reactive iron level on cardiac function and oxidative injury in the isolated rat heart. J Mol Cell Cardiol. 1996 Aug;28(8):1769-76. doi: 10.1006/jmcc.1996.0166. [PubMed:8877786  ] 
  5. LOTUS database [Link]