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Showing NP-Card for 7-methoxy-4-oxo-3h-quinoline-2-carboxylic acid (NP0225108)

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Record Information
Version2.0
Created at2022-09-06 03:44:05 UTC
Updated at2022-09-06 03:44:05 UTC
NP-MRD IDNP0225108
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-methoxy-4-oxo-3h-quinoline-2-carboxylic acid
Description7-Methoxy-4-oxo-3,4-dihydroquinoline-2-carboxylic acid belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. 7-methoxy-4-oxo-3h-quinoline-2-carboxylic acid is found in Ephedra alata. 7-Methoxy-4-oxo-3,4-dihydroquinoline-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0225108 (7-methoxy-4-oxo-3h-quinoline-2-carboxylic acid)


  Mrv1533004171500492D          

 16 17  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    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 C   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
    2.8579    0.8250    0.0000 O   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 N   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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
Download

3D MOL for NP0225108 (7-methoxy-4-oxo-3h-quinoline-2-carboxylic acid)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
    4.3678    1.3832    0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9950    1.6583    0.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9900    0.7291    0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789   -0.6029   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1939   -1.4564   -0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1034   -1.0315   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3813    0.2974    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6903    1.1720    0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7178    0.7214    0.1051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7449   -0.0618   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0563    0.5721    0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0986   -0.1294   -0.0254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2056    1.9388    0.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6607   -1.5078   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2404   -1.9308   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9330   -3.1523   -0.6003 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7508    1.4404   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8770    2.0975    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6082    0.3705    0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2966   -0.9681   -0.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4200   -2.5083   -0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4889    2.2218    0.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4795    2.5324   -0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1520   -1.6764   -1.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839   -2.1091    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 15  1  0
 15 16  2  0
 15 14  1  0
 14 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  2  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
  8  3  1  0
  7  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
 14 24  1  0
 14 25  1  0
  8 22  1  0
 13 23  1  0
M  END
Download

3D SDF for NP0225108 (7-methoxy-4-oxo-3h-quinoline-2-carboxylic acid)


  Mrv1533004171500492D          

 16 17  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    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 C   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
    2.8579    0.8250    0.0000 O   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 N   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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225108

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=O)CC(=NC2=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H9NO4/c1-16-6-2-3-7-8(4-6)12-9(11(14)15)5-10(7)13/h2-4H,5H2,1H3,(H,14,15)

> <INCHI_KEY>
XZBXJNXJRGHHOZ-UHFFFAOYSA-N

> <FORMULA>
C11H9NO4

> <MOLECULAR_WEIGHT>
219.196

> <EXACT_MASS>
219.053157774

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
21.18064336897028

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-4-oxo-3,4-dihydroquinoline-2-carboxylic acid

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
1.7431829346666663

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.470035496934162

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.780831230855991

> <JCHEM_PKA_STRONGEST_BASIC>
-4.847773474376474

> <JCHEM_POLAR_SURFACE_AREA>
75.96

> <JCHEM_REFRACTIVITY>
57.30170000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-methoxy-4-oxo-3H-quinoline-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0225108 (7-methoxy-4-oxo-3h-quinoline-2-carboxylic acid)

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PDB for NP0225108 (7-methoxy-4-oxo-3h-quinoline-2-carboxylic acid)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12    3                                                       
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0225108 (7-methoxy-4-oxo-3h-quinoline-2-carboxylic acid)
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SMILES for NP0225108 (7-methoxy-4-oxo-3h-quinoline-2-carboxylic acid)
COC1=CC=C2C(=O)CC(=NC2=C1)C(O)=O
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INCHI for NP0225108 (7-methoxy-4-oxo-3h-quinoline-2-carboxylic acid)
InChI=1S/C11H9NO4/c1-16-6-2-3-7-8(4-6)12-9(11(14)15)5-10(7)13/h2-4H,5H2,1H3,(H,14,15)
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View in JSmol
Synonyms
ValueSource
7-Methoxy-4-oxo-3,4-dihydroquinoline-2-carboxylateGenerator
Chemical FormulaC11H9NO4
Average Mass219.1960 Da
Monoisotopic Mass219.05316 Da
IUPAC Name7-methoxy-4-oxo-3,4-dihydroquinoline-2-carboxylic acid
Traditional Name7-methoxy-4-oxo-3H-quinoline-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=CC=C2C(=O)CC(=NC2=C1)C(O)=O
InChI Identifier
InChI=1S/C11H9NO4/c1-16-6-2-3-7-8(4-6)12-9(11(14)15)5-10(7)13/h2-4H,5H2,1H3,(H,14,15)
InChI KeyXZBXJNXJRGHHOZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
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
Ephedra alataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassQuinolines and derivatives  
Sub ClassQuinoline carboxylic acids  
Direct ParentQuinoline carboxylic acids  
Alternative Parents
Substituents
  • Quinoline-2-carboxylic acid
    • 

  • Dihydroquinoline
    • 

  • Anisole
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Ketimine
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Ether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic oxide
    • 

  • Imine
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP0.95ALOGPS
logP1.74ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)2.78ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area75.96 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57.3 m³·mol⁻¹ChemAxon
Polarizability21.18 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound124706308  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]