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Showing NP-Card for Benzoquinoneacetic acid (NP0086950)

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Record Information
Version2.0
Created at2022-05-11 16:35:30 UTC
Updated at2022-05-11 16:35:30 UTC
NP-MRD IDNP0086950
Secondary Accession NumbersNone
Natural Product Identification
Common NameBenzoquinoneacetic acid
DescriptionBenzoquinoneacetic acid, also known as BQA, belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. Benzoquinoneacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzoquinoneacetic acid is a potentially toxic compound. Benzoquinoneacetic acid (BQA) is an oxidized form of homogentisic acid. More specifically, Benzoquinoneacetic acid can form polymers that resemble the dark skin pigment melanin. Benzoquinoneacetic acid was first documented in 1987 (PMID: 3121448). Chronically high levels of Benzoquinoneacetic acid are associated with alkaptonuria (OMIM: 203500 ), An inborn error of metabolism.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086950 (Benzoquinoneacetic acid)

            3-Hydroxyphenylglycine.mol
  Mrv1652303211819022D          

 12 12  0  0  0  0            999 V2000
   -1.7862    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.4125    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  6  7  2  0  0  0  0
  3  8  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for NP0086950 (Benzoquinoneacetic acid)

     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.6542    1.0816   -2.4335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218    0.6493   -1.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7456    0.0045   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1051   -0.4480    0.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585   -0.3120    0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -0.7294    1.8286 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1047    0.3226   -0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5592    0.4456   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2520   -0.8607   -0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6906   -1.9658   -0.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6429   -0.8205    0.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5687    0.7672   -1.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8178   -0.0819   -0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6481   -0.9142    1.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8918    1.0604    0.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9637    0.9552   -1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051   -0.3950    0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0099    1.2411   -2.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  1  0
  7 12  2  0
 12  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
 11 17  1  0
  8 15  1  0
  8 16  1  0
 12 18  1  0
  3 13  1  0
  4 14  1  0
M  END
Download

3D SDF for NP0086950 (Benzoquinoneacetic acid)

            3-Hydroxyphenylglycine.mol
  Mrv1652303211819022D          

 12 12  0  0  0  0            999 V2000
   -1.7862    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.4125    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  6  7  2  0  0  0  0
  3  8  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086950

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H6O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3H,4H2,(H,11,12)

> <INCHI_KEY>
RAPRJRLALQKSHB-UHFFFAOYSA-N

> <FORMULA>
C8H6O4

> <MOLECULAR_WEIGHT>
166.1308

> <EXACT_MASS>
166.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.582014124643841

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,6-dioxocyclohexa-1,4-dien-1-yl)acetic acid

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
0.5439912006666665

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.876752047836376

> <JCHEM_PKA_STRONGEST_BASIC>
-8.471923452091904

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
41.652300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzoquinoneacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0086950 (Benzoquinoneacetic acid)

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PDB for NP0086950 (Benzoquinoneacetic acid)
HEADER    PROTEIN                                 21-MAR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:             3-Hydroxyphenylglycine.mol            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-MAR-18         0                                  
HETATM    1  C   UNK     0      -3.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.667   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.001   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.001   3.080   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.001  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.001   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.334   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    3                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0086950 (Benzoquinoneacetic acid)
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SMILES for NP0086950 (Benzoquinoneacetic acid)
OC(=O)CC1=CC(=O)C=CC1=O
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INCHI for NP0086950 (Benzoquinoneacetic acid)
InChI=1S/C8H6O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3H,4H2,(H,11,12)
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View in JSmol
Synonyms
ValueSource
BenzoquinoneacetateGenerator
BQAHMDB
Benzoquinone acetic acidHMDB
2-(3,6-Dioxocyclohexa-1,4-dien-1-yl)acetateHMDB
Chemical FormulaC8H6O4
Average Mass166.1308 Da
Monoisotopic Mass166.02661 Da
IUPAC Name2-(3,6-dioxocyclohexa-1,4-dien-1-yl)acetic acid
Traditional Namebenzoquinoneacetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CC(=O)C=CC1=O
InChI Identifier
InChI=1S/C8H6O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3H,4H2,(H,11,12)
InChI KeyRAPRJRLALQKSHB-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 p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentP-benzoquinones  
Alternative Parents
Substituents
  • P-benzoquinone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP0.41ALOGPS
logP0.54ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.88ChemAxon
pKa (Strongest Basic)-8.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.65 m³·mol⁻¹ChemAxon
Polarizability14.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002334  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022966  
KNApSAcK IDNot Available
Chemspider ID13628337  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6628  
PubChem Compound21252288  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Martin JP Jr, Batkoff B: Homogentisic acid autoxidation and oxygen radical generation: implications for the etiology of alkaptonuric arthritis. Free Radic Biol Med. 1987;3(4):241-50. doi: 10.1016/s0891-5849(87)80031-x. [PubMed:3121448  ]