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Showing Compound homogentisate (FDB030907)

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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
Physico-Chemical Properties - Experimental
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-0900000000-9c395aa569b4b54f86812012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00xs-9500000000-ab92286f0d5bc843814b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-35740a40f4fdf3e84c3c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-f4eba60d63bd99e18b8b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-12e330dc18f0b128b9612012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-0900000000-4bd53b0472edd31e86092012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-0900000000-7121173193a9ba3751a42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-1900000000-04eca21bf25c671b8b6e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-0900000000-780d3740762c2ff89d9a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-f4eba60d63bd99e18b8b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-12e330dc18f0b128b9612017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-4bd53b0472edd31e86092017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-7121173193a9ba3751a42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-04eca21bf25c671b8b6e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0900000000-9c85164306514c6d4c4b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-867a4e32ba2d14fd0aad2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-ac8e05a9300b51b24e772021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-1900000000-eeb664cef1197d6097352021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-1d890267ec7f3a5843b32021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0900000000-a650bbb95019f3305d032017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-94f13b2c7b97263537012017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tf-9300000000-968a6390a00dcd77e5662017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-0f9d5926d702af7d4d632017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-7f257033d3b1952b3c272017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-bbcb0f0d7348cd1663b12017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
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