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Human Metabolome Database Version 3.5

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Showing metabocard for Benzoquinoneacetic acid (HMDB02334)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:48 -0600
Update Date 2013-02-08 17:11:45 -0700
HMDB ID HMDB02334
Secondary Accession Numbers None
Metabolite Identification
Common Name Benzoquinoneacetic acid
Description Benzoquinoneacetic acid is an oxidized phase of the oxidation-reduction system homogentisic-benzoquinoneacetic acid. This compound is secreted in large quantities in the urine of patients suffering from cyanosis. Cyanosis is the bluish coloration of the skin due to the presence of deoxygenated hemoglobin in blood vessels near the skin surface. (Ella H. Fishberg, J. Biol. Chem., Jan 1948; 172: 155 - 163; Wikipedia).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Benzoquinoneacetate
  2. BQA
Chemical Formula C8H6O4
Average Molecular Weight 166.1308
Monoisotopic Molecular Weight 166.02660868
IUPAC Name 2-(3,6-dioxocyclohexa-1,4-dien-1-yl)acetic acid
Traditional IUPAC Name (3,6-dioxocyclohexa-1,4-dien-1-yl)acetic acid
CAS Registry Number 10275-07-7
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 Key RAPRJRLALQKSHB-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Homomonocyclic Compounds
Class Benzoquinones
Sub Class N/A
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
Substituents
  • Carboxylic Acid
  • Ketone
Direct Parent Benzoquinones
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 5.46 g/L ALOGPS
LogP 0.41 ALOGPS
LogP 0.54 ChemAxon
LogS -1.48 ALOGPS
pKa (strongest acidic) 3.88 ChemAxon
pKa (strongest basic) -8.5 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 71.44 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 41.65 ChemAxon
Polarizability 14.64 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022966
KNApSAcK ID Not Available
Chemspider ID 13628337 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02334 Link_out
Metagene Link HMDB02334 Link_out
METLIN ID 6628 Link_out
PubChem Compound 21252288 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not 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 Link_out
  2. FISHBERG EH. Excretion of benzoquinoneacetic acid in hypovitaminosis C. J Biol Chem. 1948 Jan;172(1):155-63.