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Showing NP-Card for 2-Quinolone (NP0079721)

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Record Information
Version2.0
Created at2022-04-29 00:45:27 UTC
Updated at2022-04-29 00:45:27 UTC
NP-MRD IDNP0079721
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Quinolone
Description2-Hydroxyquinoline, also known as 2-chinolinol or quinolin-2(1H)-one, belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. 2-Quinolone is found in Aconitum ferox, Glycosmis arborea, Glycosmis pentaphylla and Houttuynia cordata. 2-Quinolone was first documented in 2010 (PMID: 19856115). 2-Hydroxyquinoline is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 21558655).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0079721 (2-Quinolone)


  Mrv1652304021923432D          

 11 12  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -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
    3.5724   -0.4125    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
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
M  END
Download

3D MOL for NP0079721 (2-Quinolone)

     RDKit          3D

 18 19  0  0  0  0  0  0  0  0999 V2000
   -3.2711   -1.3027   -0.9183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -0.6526   -0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3073    0.7251   -0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1629    1.4255   -0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276    0.6993    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1416    1.3501    0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2874    0.6443    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3184   -0.7352    0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501   -1.3913    0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0022   -0.6883   -0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352   -1.3485   -0.3289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2325    1.2521   -0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1655    2.5130   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1196    2.4480    0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1777    1.2109    0.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2276   -1.2859    0.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1879   -2.4722    0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0816   -2.3916   -0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2 11  1  0
 11 10  1  0
 10  9  2  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 10  1  0
 11 18  1  0
  9 17  1  0
  8 16  1  0
  7 15  1  0
  6 14  1  0
  4 13  1  0
  3 12  1  0
M  END
Download

3D SDF for NP0079721 (2-Quinolone)


  Mrv1652304021923432D          

 11 12  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -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
    3.5724   -0.4125    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
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079721

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1NC2=CC=CC=C2C=C1

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

> <INCHI_KEY>
LISFMEBWQUVKPJ-UHFFFAOYSA-N

> <FORMULA>
C9H7NO

> <MOLECULAR_WEIGHT>
145.158

> <EXACT_MASS>
145.052763851

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.82129022770586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2-dihydroquinolin-2-one

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
1.5971423416666664

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.952454233112086

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1866847715175437

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
45.2792

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-oxoquinoline

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0079721 (2-Quinolone)

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PDB for NP0079721 (2-Quinolone)
HEADER    PROTEIN                                 02-APR-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-19         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0079721 (2-Quinolone)
Download
SMILES for NP0079721 (2-Quinolone)
O=C1NC2=CC=CC=C2C=C1
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INCHI for NP0079721 (2-Quinolone)
InChI=1S/C9H7NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h1-6H,(H,10,11)
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View in JSmol
Synonyms
ValueSource
2-ChinolinolChEBI
2-QuinolinolChEBI
Quinolin-2(1H)-oneKegg
2-HydroxyquinolineChEBI
Chemical FormulaC9H7NO
Average Mass145.1580 Da
Monoisotopic Mass145.05276 Da
IUPAC Name1,2-dihydroquinolin-2-one
Traditional Name2-oxoquinoline
CAS Registry NumberNot Available
SMILES
O=C1NC2=CC=CC=C2C=C1
InChI Identifier
InChI=1S/C9H7NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h1-6H,(H,10,11)
InChI KeyLISFMEBWQUVKPJ-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
Aconitum feroxLOTUS Database
Glycosmis arboreaPlant
Glycosmis pentaphyllaLOTUS Database
Houttuynia cordataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassQuinolines and derivatives  
Sub ClassQuinolones and derivatives  
Direct ParentHydroquinolones  
Alternative Parents
Substituents
  • Dihydroquinolone
    • 

  • Dihydroquinoline
    • 

  • Pyridinone
    • 

  • Pyridine
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Lactam
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen 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
logP1.51ALOGPS
logP1.6ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)13.95ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.28 m³·mol⁻¹ChemAxon
Polarizability14.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0240308  
DrugBank IDDB04745  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00044432  
Chemspider IDNot Available
KEGG Compound IDC06415  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link8-Hydroxyquinoline  
METLIN IDNot Available
PubChem Compound6038  
PDB IDNot Available
ChEBI ID16365  
Good Scents IDNot Available
References
General References
  1. Bai Y, Sun Q, Zhao C, Wen D, Tang X: Quinoline biodegradation and its nitrogen transformation pathway by a Pseudomonas sp. strain. Biodegradation. 2010 Jun;21(3):335-44. doi: 10.1007/s10532-009-9304-9. Epub 2009  Oct 24. [PubMed:19856115  ] 
  2. Deng X, Chai X, Wei C, Fu L: Rapid determination of quinoline and 2-hydroxyquinoline in quinoline biodegradation process by tri-wavelength UV/Vis spectroscopy. Anal Sci. 2011;27(5):493. doi: 10.2116/analsci.27.493. [PubMed:21558655  ]