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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2023-02-21 17:16:21 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
Thumb
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
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
Predicted Chromatographic Properties
Spectra
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.. .