You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2019-10-11 15:19:01 UTC
Update Date2019-10-16 15:41:01 UTC
HMDB IDHMDB0240526
Secondary Accession NumbersNone
Metabolite Identification
Common NameHomovanillic acid 4-glucuronide
DescriptionHomovanillic acid 4-glucuronide belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Homovanillic acid 4-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
Homovanillate 4-glucuronideGenerator
4-(Carboxymethyl)-2-methoxyphenyl b-D-glucopyranosiduronateGenerator
4-(Carboxymethyl)-2-methoxyphenyl b-D-glucopyranosiduronic acidGenerator
4-(Carboxymethyl)-2-methoxyphenyl beta-D-glucopyranosiduronateGenerator
4-(Carboxymethyl)-2-methoxyphenyl β-D-glucopyranosiduronateGenerator
4-(Carboxymethyl)-2-methoxyphenyl β-D-glucopyranosiduronic acidGenerator
(4-Hydroxy-3-methoxyphenyl)acetic acid glucuronideHMDB
3'-Methoxy-4'-hydroxyphenylacetic acid glucuronideHMDB
3-Methoxy-4-hydroxyphenylacetic acid glucuronideHMDB
3’-Methoxy-4’-hydroxyphenylacetic acid glucuronideHMDB
4-Hydroxy-3-methoxybenzeneacetic acid glucuronideHMDB
Homovanillic acid glucuronideHMDB
Vanilacetic acid glucuronideHMDB
(2S,3S,4S,5R,6S)-6-[4-(Carboxymethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Chemical FormulaC15H18O10
Average Molecular Weight358.299
Monoisotopic Molecular Weight358.08999678
IUPAC Name(2S,3S,4S,5R,6S)-6-[4-(carboxymethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-[4-(carboxymethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]1(OC2=C(OC)C=C(CC(O)=O)C=C2)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O
InChI Identifier
InChI=1S/C15H18O10/c1-23-8-4-6(5-9(16)17)2-3-7(8)24-15-12(20)10(18)11(19)13(25-15)14(21)22/h2-4,10-13,15,18-20H,5H2,1H3,(H,16,17)(H,21,22)/t10-,11-,12+,13-,15+/m0/s1
InChI KeyCXBMXYMXMRBMJY-DKBOKBLXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Hydroxy acid
  • Monosaccharide
  • Pyran
  • Oxane
  • Secondary alcohol
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Oxacycle
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.63ALOGPS
logP-0.8ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.98 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity77.82 m³·mol⁻¹ChemAxon
Polarizability32.96 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05o3-0719000000-04c2aa401d187d101e1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m0-0901000000-fd19e38e717e7659857bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-1900000000-76a864d8bf55ca411d80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bu0-0529000000-9d5b5be82367981e141cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1922000000-5ea02bf9a3f7a5a24d40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-2900000000-c39d968948f2d3b18b29Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB093719
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound122372628
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available