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Record Information
Version1.0
Creation Date2016-09-30 22:19:57 UTC
Update Date2020-05-21 16:28:38 UTC
MCDB ID BMDB0000130
Secondary Accession Numbers
  • BMDB00130
Metabolite Identification
Common NameHomogentisic acid
DescriptionHomogentisic acid, also known as homogentisate or acid, homogentisic, 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. Homogentisic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Homogentisic acid exists in all living organisms, ranging from bacteria to humans. Homogentisic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-(2,5-dihydroxyphenyl)acetic acid
Traditional Namehomogentisic acid
CAS Registry Number451-13-8
SMILES
OC(=O)CC1=C(O)C=CC(O)=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point153 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility850 mg/mL at 25 °CNot Available
LogP0.86SANGSTER (1994)
Predicted Properties
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000130
DrugBank IDDB08327
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030907
KNApSAcK IDC00007309
Chemspider ID759
KEGG Compound IDC00544
BioCyc IDHOMOGENTISATE
BiGG ID1485308
Wikipedia LinkHomogentisic_acid
METLIN ID331
PubChem Compound780
PDB IDNot Available
ChEBI ID44747
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]