Record Information
Version1.0
Creation date2011-09-21 00:22:30 UTC
Update date2015-07-21 06:57:27 UTC
Primary IDFDB022966
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBenzoquinoneacetic acid
DescriptionBenzoquinoneacetic 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) [HMDB]
CAS Number10275-07-7
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility5.46 g/LALOGPS
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
Chemical FormulaC8H6O4
IUPAC name2-(3,6-dioxocyclohexa-1,4-dien-1-yl)acetic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)CC1=CC(=O)C=CC1=O
Average Molecular Weight166.1308
Monoisotopic Molecular Weight166.02660868
Classification
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:

Role

Indirect biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBenzoquinoneacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6900000000-51321079231d86b295a3Spectrum
Predicted GC-MSBenzoquinoneacetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8920000000-6c81edffefa422ba173aSpectrum
Predicted GC-MSBenzoquinoneacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBenzoquinoneacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-fa130465e081632f69f12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-4900000000-cd386239c5244d6527df2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0690-9000000000-db1f626a086c73a6579e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-8b51337fe9bfda05eb612017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-0900000000-9afdadb1210637bd69a52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-9700000000-6f354928322b23cc865b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-a28fdef9c1c00d45c3ff2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-6a3b331dfd30a9e6f27b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xu-9500000000-a79dd2db9080267331812021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-c9641136c29dd50408632021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-ee5a7e2a4027680d79ed2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l6u-9300000000-52241a6448ab82fb7f182021-09-22View Spectrum
NMRNot Available
ChemSpider ID13628337
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID21252288
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02334
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference