Record Information
Version1.0
Creation date2015-05-07 20:29:17 UTC
Update date2019-11-26 03:21:56 UTC
Primary IDFDB030907
Secondary Accession Numbers
  • FDB021899
Chemical Information
FooDB Namehomogentisate
Description2-(3,6-dihydroxyphenyl)acetic acid, also known as homogentisic acid or homogentisate, is a member of the class of compounds known as 2(hydroxyphenyl)acetic acids. 2(hydroxyphenyl)acetic acids are phenylacetic acids that carry a hydroxyl group at the 2-position. 2-(3,6-dihydroxyphenyl)acetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-(3,6-dihydroxyphenyl)acetic acid can be found in a number of food items such as gooseberry, angelica, chinese broccoli, and cucumber, which makes 2-(3,6-dihydroxyphenyl)acetic acid a potential biomarker for the consumption of these food products. 2-(3,6-dihydroxyphenyl)acetic acid can be found primarily in blood, feces, and urine, as well as in human cartilage, connective tissue and kidney tissues. In humans, 2-(3,6-dihydroxyphenyl)acetic acid is involved in few metabolic pathways, which include disulfiram action pathway, phenylalanine and tyrosine metabolism, and tyrosine metabolism. 2-(3,6-dihydroxyphenyl)acetic acid is also involved in several metabolic disorders, some of which include dopamine beta-hydroxylase deficiency, tyrosinemia type 3 (TYRO3), alkaptonuria, and tyrosinemia type 2 (or richner-hanhart syndrome). Moreover, 2-(3,6-dihydroxyphenyl)acetic acid is found to be associated with alkaptonuria. 2-(3,6-dihydroxyphenyl)acetic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Apart from treatment of the complications (such as pain relief using NSAIDs and joint replacement for the cartilage damage), vitamin C has been used to reduce the ochronosis and lowering of the homogentisic acid levels may be attempted with a low-protein diet. Recently the drug nitisinone has been found to suppress homogentisic acid production. Nitrisinone inhibits the enzyme, 4-hydroxyphenylpyruvate dioxygenase, responsible for converting tyrosine to homogentisic acid, thereby blocking the production and accumulation of homogentisic acid. Nitisinone treatment has been shown to cause a 95% reduction in plasma and urinary homogentisic acid (T3DB).
CAS Number451-13-8
Structure
Thumb
Synonyms
SynonymSource
2,5-Dihydroxyphenylacetic acidChEBI
2-(3,6-DIHYDROXYPHENYL)acetIC ACIDChEBI
2,5-DihydroxyphenylacetateKegg
2-(3,6-DIHYDROXYPHENYL)acetateGenerator
HomogentisateGenerator
(2,5-Dihydroxyphenyl)-acetateHMDB
(2,5-Dihydroxyphenyl)-acetic acidHMDB
2,5-Dihydroxy-a-toluateHMDB
2,5-Dihydroxy-a-toluic acidHMDB
2,5-Dihydroxy-alpha-toluateHMDB
2,5-Dihydroxy-alpha-toluic acidHMDB
2,5-Dihydroxy-benzeneacetateHMDB
2,5-Dihydroxy-benzeneacetic acidHMDB
AlcaptonHMDB
Homogentisate acidHMDB
HomogentisinateHMDB
Homogentisinic acidHMDB
Melanic acidHMDB
Acid, homogentisicHMDB
Predicted Properties
PropertyValueSource
Water Solubility8.1 g/LALOGPS
logP0.81ALOGPS
logP1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability15.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O4
IUPAC name2-(2,5-dihydroxyphenyl)acetic acid
InChI IdentifierInChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
InChI KeyIGMNYECMUMZDDF-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC1=C(O)C=CC(O)=C1
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
Classification
Description Belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acids
Direct Parent2(hydroxyphenyl)acetic acids
Alternative Parents
Substituents
  • 2(hydroxyphenyl)acetic acid
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSHomogentisic acid, non-derivatized, GC-MS Spectrumsplash10-000t-0945000000-2f4b9ef9c9ee6e7cd1edSpectrum
GC-MSHomogentisic acid, 3 TMS, GC-MS Spectrumsplash10-0016-3955000000-1cdc64ab3032ff29df29Spectrum
GC-MSHomogentisic acid, non-derivatized, GC-MS Spectrumsplash10-0a5c-0679000000-97890865f85a79efa2e6Spectrum
GC-MSHomogentisic acid, non-derivatized, GC-MS Spectrumsplash10-000t-0945000000-2f4b9ef9c9ee6e7cd1edSpectrum
GC-MSHomogentisic acid, non-derivatized, GC-MS Spectrumsplash10-0016-3955000000-1cdc64ab3032ff29df29Spectrum
GC-MSHomogentisic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0944000000-fd48cc27da661ce24833Spectrum
Predicted GC-MSHomogentisic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-4900000000-ea40fc8d43156151710cSpectrum
Predicted GC-MSHomogentisic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-5093000000-c342ba08a9bff049fc1cSpectrum
Predicted GC-MSHomogentisic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomogentisic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-9c395aa569b4b54f8681Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00xs-9500000000-ab92286f0d5bc843814bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-35740a40f4fdf3e84c3cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-f4eba60d63bd99e18b8bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-12e330dc18f0b128b961Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-0900000000-4bd53b0472edd31e8609Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-0900000000-7121173193a9ba3751a4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-1900000000-04eca21bf25c671b8b6eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-0900000000-780d3740762c2ff89d9aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-f4eba60d63bd99e18b8bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-12e330dc18f0b128b961Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-4bd53b0472edd31e8609Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-7121173193a9ba3751a4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-04eca21bf25c671b8b6eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0900000000-9c85164306514c6d4c4bSpectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-867a4e32ba2d14fd0aadSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-ac8e05a9300b51b24e77Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-1900000000-eeb664cef1197d609735Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-1d890267ec7f3a5843b3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0900000000-a650bbb95019f3305d03Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-94f13b2c7b9726353701Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tf-9300000000-968a6390a00dcd77e566Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-0f9d5926d702af7d4d63Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-7f257033d3b1952b3c27Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-bbcb0f0d7348cd1663b1Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
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
FoodReference
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