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Showing NP-Card for quinolacetic acid (NP0245710)

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Record Information
Version2.0
Created at2022-09-07 06:53:23 UTC
Updated at2022-09-07 06:53:23 UTC
NP-MRD IDNP0245710
Secondary Accession NumbersNone
Natural Product Identification
Common Namequinolacetic acid
DescriptionQuinolacetic acid, also known as quinolacetate, belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). Quinolacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Quinolacetic acid is a potentially toxic compound. quinolacetic acid is found in Ajuga parviflora. Quinolacetic acid is a metabolite associated with Hawkinsinuria.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0245710 (quinolacetic acid)


  Mrv1652302281821312D          

 12 12  0  0  0  0            999 V2000
10001.351310001.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.066010000.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.780910001.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.066010000.0152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.637410001.6636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4967 9999.6040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.924510001.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.210010000.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.210010000.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9245 9999.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.639010000.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.639010000.8400    0.0000 C   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
  2  4  2  0  0  0  0
  7  8  2  0  0  0  0
  8  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
 12  7  1  0  0  0  0
  9  6  2  0  0  0  0
 12  5  1  0  0  0  0
  1 12  1  0  0  0  0
M  END
Download

3D MOL for NP0245710 (quinolacetic acid)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.8050    0.5420   -0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947    0.2701   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1189   -0.9791    0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337   -1.1599    0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081   -0.1533    0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270    0.1410    1.4759 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2704   -0.8311   -0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    0.0177   -0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078   -0.3517   -1.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5103    1.2392   -0.1539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    1.0768   -0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6166    1.3181   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8177   -1.7424    0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4646   -2.0948    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559    0.2139    2.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -1.2408   -1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930   -1.7263    0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9287    1.3249    0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3450    1.8668   -0.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9693    2.2690   -0.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 12  1  0
 12 11  2  0
 11  5  1  0
 10 18  1  0
  7 16  1  0
  7 17  1  0
  6 15  1  0
  4 14  1  0
  3 13  1  0
 12 20  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0245710 (quinolacetic acid)


  Mrv1652302281821312D          

 12 12  0  0  0  0            999 V2000
10001.351310001.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.066010000.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.780910001.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.066010000.0152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.637410001.6636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4967 9999.6040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.924510001.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.210010000.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.210010000.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9245 9999.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.639010000.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.639010000.8400    0.0000 C   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
  2  4  2  0  0  0  0
  7  8  2  0  0  0  0
  8  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
 12  7  1  0  0  0  0
  9  6  2  0  0  0  0
 12  5  1  0  0  0  0
  1 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245710

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1(O)C=CC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c9-6-1-3-8(12,4-2-6)5-7(10)11/h1-4,12H,5H2,(H,10,11)

> <INCHI_KEY>
RFJUCKOEXRTZPN-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.148

> <EXACT_MASS>
168.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.024644137915034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetic acid

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
0.04770239533333312

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.953810531470687

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.065688409320586

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3819778395846116

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
42.4691

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.67e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0245710 (quinolacetic acid)

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PDB for NP0245710 (quinolacetic acid)
HEADER    PROTEIN                                 28-FEB-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-FEB-18         0                                  
HETATM    1  C   UNK     0    8669.1898669.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8670.5238668.234   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8671.8588669.003   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8670.5238666.695   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8667.8578669.772   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8663.8608665.927   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8666.5268669.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1928668.235   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.1928666.694   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.5268665.924   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8608666.694   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.8608668.235   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5   12                                                            
CONECT    6    9                                                            
CONECT    7    8   12                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    6                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7    5    1                                             
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0245710 (quinolacetic acid)
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SMILES for NP0245710 (quinolacetic acid)
OC(=O)CC1(O)C=CC(=O)C=C1
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INCHI for NP0245710 (quinolacetic acid)
InChI=1S/C8H8O4/c9-6-1-3-8(12,4-2-6)5-7(10)11/h1-4,12H,5H2,(H,10,11)
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View in JSmol
Synonyms
ValueSource
QuinolacetateGenerator
Chemical FormulaC8H8O4
Average Mass168.1480 Da
Monoisotopic Mass168.04226 Da
IUPAC Name2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetic acid
Traditional Name(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1(O)C=CC(=O)C=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-1-3-8(12,4-2-6)5-7(10)11/h1-4,12H,5H2,(H,10,11)
InChI KeyRFJUCKOEXRTZPN-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
Ajuga parvifloraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct ParentTertiary alcohols  
Alternative Parents
Substituents
  • Tertiary alcohol
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP-0.2ALOGPS
logP0.048ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)4.07ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.47 m³·mol⁻¹ChemAxon
Polarizability15.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0240257  
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 LinkQuinolacetic acid  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]