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Showing NP-Card for 4,6-Dihydroxyquinoline (NP0087133)

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Record Information
Version2.0
Created at2022-05-11 16:41:02 UTC
Updated at2022-05-11 16:41:02 UTC
NP-MRD IDNP0087133
Secondary Accession NumbersNone
Natural Product Identification
Common Name4,6-Dihydroxyquinoline
Description4,6-Dihydroxyquinoline, also known as quinoline-4,6-diol or 4,6-quinolinediol, belongs to the class of organic compounds known as hydroxyquinolones. Hydroxyquinolones are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. Quinoline substituted by hydroxy groups at the 4- and 6-positions. 4,6-Dihydroxyquinoline is a moderately basic compound (based on its pKa). 4,6-Dihydroxyquinoline exists in all living organisms, ranging from bacteria to humans. 4,6-Dihydroxyquinoline can be biosynthesized from 5-hydroxykynurenamine; which is mediated by the enzyme kynurenine 3-monooxygenase. In humans, 4,6-dihydroxyquinoline is involved in tryptophan metabolism.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087133 (4,6-Dihydroxyquinoline)


  Mrv0541 02231219522D          

 12 13  0  0  0  0            999 V2000
   13.0363  -10.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0363  -10.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7508  -11.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4653  -10.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4653  -10.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7508   -9.7212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1797  -11.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8942  -10.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8942  -10.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1797   -9.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7508  -12.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6087  -11.3712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  3 11  1  0  0  0  0
  8 12  1  0  0  0  0
M  END
Download

3D MOL for NP0087133 (4,6-Dihydroxyquinoline)

     RDKit          3D

 19 20  0  0  0  0  0  0  0  0999 V2000
    3.1604    1.4434   -0.0783 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0780    0.5937   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2550   -0.7565    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1975   -1.6263    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0855   -1.1244    0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1396   -1.9587    0.0487 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3935   -1.4938    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6707   -0.1476   -0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6196    0.7367   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8957    2.0698   -0.1807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3317    0.2553   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    1.0790   -0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6089    1.8478    0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2697   -1.1442    0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407   -2.6901    0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026   -2.2090    0.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215    0.1819   -0.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2237    2.7977   -0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012    2.1453   -0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 12  2  0
 12 11  1  0
 11  9  2  0
  9 10  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  5 11  1  0
  1 13  1  0
 12 19  1  0
 10 18  1  0
  8 17  1  0
  7 16  1  0
  4 15  1  0
  3 14  1  0
M  END
Download

3D SDF for NP0087133 (4,6-Dihydroxyquinoline)


  Mrv0541 02231219522D          

 12 13  0  0  0  0            999 V2000
   13.0363  -10.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0363  -10.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7508  -11.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4653  -10.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4653  -10.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7508   -9.7212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1797  -11.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8942  -10.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8942  -10.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1797   -9.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7508  -12.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6087  -11.3712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  3 11  1  0  0  0  0
  8 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(O)C=CN=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO2/c11-6-1-2-8-7(5-6)9(12)3-4-10-8/h1-5,11H,(H,10,12)

> <INCHI_KEY>
XFALURCRIGINGT-UHFFFAOYSA-N

> <FORMULA>
C9H7NO2

> <MOLECULAR_WEIGHT>
161.1574

> <EXACT_MASS>
161.047678473

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
15.802360004009294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
quinoline-4,6-diol

> <ALOGPS_LOGP>
1.09

> <JCHEM_LOGP>
1.5237698280000003

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.752738042109634

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.510163396199507

> <JCHEM_PKA_STRONGEST_BASIC>
2.8369265667790615

> <JCHEM_POLAR_SURFACE_AREA>
53.35000000000001

> <JCHEM_REFRACTIVITY>
43.94109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dihydroxyquinoline

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0087133 (4,6-Dihydroxyquinoline)

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PDB for NP0087133 (4,6-Dihydroxyquinoline)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      24.334 -18.916   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.334 -20.456   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.668 -21.226   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.002 -20.456   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.002 -18.916   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      25.668 -18.146   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      28.335 -21.226   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.669 -20.456   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.669 -18.916   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.335 -18.146   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      25.668 -22.766   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      31.003 -21.226   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    3                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0087133 (4,6-Dihydroxyquinoline)
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SMILES for NP0087133 (4,6-Dihydroxyquinoline)
OC1=CC2=C(O)C=CN=C2C=C1
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INCHI for NP0087133 (4,6-Dihydroxyquinoline)
InChI=1S/C9H7NO2/c11-6-1-2-8-7(5-6)9(12)3-4-10-8/h1-5,11H,(H,10,12)
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View in JSmol
Synonyms
ValueSource
6-Hydroxy-1H-quinolin-4-oneChEBI
Quinoline-4,6-diolKegg
4,6-QuinolinediolHMDB
Chemical FormulaC9H7NO2
Average Mass161.1574 Da
Monoisotopic Mass161.04768 Da
IUPAC Namequinoline-4,6-diol
Traditional Name4,6-dihydroxyquinoline
CAS Registry NumberNot Available
SMILES
OC1=CC2=C(O)C=CN=C2C=C1
InChI Identifier
InChI=1S/C9H7NO2/c11-6-1-2-8-7(5-6)9(12)3-4-10-8/h1-5,11H,(H,10,12)
InChI KeyXFALURCRIGINGT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyquinolones. Hydroxyquinolones are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassQuinolines and derivatives  
Sub ClassQuinolones and derivatives  
Direct ParentHydroxyquinolones  
Alternative Parents
Substituents
  • Hydroxyquinolone
    • 

  • Dihydroquinolone
    • 

  • Hydroxyquinoline
    • 

  • Dihydroquinoline
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyridine
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous amide
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen 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
logP1.09ALOGPS
logP1.52ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)2.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.35 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.94 m³·mol⁻¹ChemAxon
Polarizability15.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004077  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023301  
KNApSAcK IDNot Available
Chemspider ID389609  
KEGG Compound IDC05639  
BioCyc IDNot Available
BiGG ID46176  
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440738  
PDB IDNot Available
ChEBI ID28799  
Good Scents IDNot Available
References
General ReferencesNot Available