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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2020-02-26 21:24:04 UTC
HMDB IDHMDB0002334
Secondary Accession Numbers
  • HMDB02334
Metabolite Identification
Common NameBenzoquinoneacetic acid
DescriptionBenzoquinoneacetic acid (BQA) is an oxidized form of homogentisic acid. The oxidation of homogentisic acid to BQA is catalyzed by the enzyme polyphenol oxidase. BQA is secreted in high quantities in the urine of patients suffering from cyanosis caused by vitamin C deficiency (Ella H. Fishberg, J. Biol. Chem., Jan 1948; 172: 155 - 163). Cyanosis is the bluish colouration of the skin due to the presence of deoxygenated hemoglobin in blood vessels near the skin surface. When present in sufficiently high levels, BQA can function as an osteotoxin and a renal toxin. An osteotoxin is a substance that causes damage to bones and/or joints. A renal toxin causes damage to the kidneys. Chronically high levels of BQA are associated with alkaptonuria (OMIM: 203500 ), an inborn error of metabolism. Alkaptonuria is a rare inherited genetic disorder in which the body cannot process the amino acids phenylalanine and tyrosine. It is caused by a mutation in the enzyme homogentisate 1,2-dioxygenase (EC 1.13.11.5), which leads to an accumulation of both homogentisic acid and BQA in the blood and tissues. When excreted in the urine, these compounds give it an unusually dark color. The accumulating BQA causes damage to cartilage (ochronosis, leading to osteoarthritis) and heart valves as well as precipitating as kidney stones and stones in other organs. More specifically, BQA can form polymers that resemble the dark skin pigment melanin. These are deposited in collagen, especially in tissues such as cartilage. This process is called ochronosis (as the tissue looks ochre); ochronotic tissue is stiffened and unusually brittle, impairing its normal function and causing damage.
Structure
Data?1582752244
Synonyms
ValueSource
BenzoquinoneacetateGenerator
BQAHMDB
Benzoquinone acetic acidHMDB
2-(3,6-Dioxocyclohexa-1,4-dien-1-yl)acetateGenerator, HMDB
Chemical FormulaC8H6O4
Average Molecular Weight166.1308
Monoisotopic Molecular Weight166.02660868
IUPAC Name2-(3,6-dioxocyclohexa-1,4-dien-1-yl)acetic acid
Traditional Namebenzoquinoneacetic acid
CAS Registry Number10275-07-7
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
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
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.46 g/LALOGPS
logP10(0.41) g/LALOGPS
logP10(0.54) g/LChemAxon
logS10(-1.5) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.19231661259
DarkChem[M-H]-132.63131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzoquinoneacetic acidOC(=O)CC1=CC(=O)C=CC1=O2883.4Standard polar33892256
Benzoquinoneacetic acidOC(=O)CC1=CC(=O)C=CC1=O1303.2Standard non polar33892256
Benzoquinoneacetic acidOC(=O)CC1=CC(=O)C=CC1=O1511.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzoquinoneacetic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC(=O)C=CC1=O1772.4Semi standard non polar33892256
Benzoquinoneacetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC(=O)C=CC1=O2027.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzoquinoneacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-51321079231d86b295a32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoquinoneacetic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8920000000-6c81edffefa422ba173a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoquinoneacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoquinoneacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 10V, Positive-QTOFsplash10-0002-0900000000-fa130465e081632f69f12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 20V, Positive-QTOFsplash10-00dj-4900000000-cd386239c5244d6527df2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 40V, Positive-QTOFsplash10-0690-9000000000-db1f626a086c73a6579e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 10V, Negative-QTOFsplash10-01b9-0900000000-8b51337fe9bfda05eb612017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 20V, Negative-QTOFsplash10-00xs-0900000000-9afdadb1210637bd69a52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 40V, Negative-QTOFsplash10-014j-9700000000-6f354928322b23cc865b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 10V, Negative-QTOFsplash10-00di-0900000000-a28fdef9c1c00d45c3ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 20V, Negative-QTOFsplash10-00di-0900000000-6a3b331dfd30a9e6f27b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 40V, Negative-QTOFsplash10-00xu-9500000000-a79dd2db9080267331812021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 10V, Positive-QTOFsplash10-00di-0900000000-c9641136c29dd50408632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 20V, Positive-QTOFsplash10-00di-2900000000-ee5a7e2a4027680d79ed2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoquinoneacetic acid 40V, Positive-QTOFsplash10-0l6u-9300000000-52241a6448ab82fb7f182021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. [PubMed:3121448 ]
  2. (). FISHBERG EH. Excretion of benzoquinoneacetic acid in hypovitaminosis C. J Biol Chem. 1948 Jan;172(1):155-63.. .