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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-17 22:11:29 UTC
Update Date2019-11-12 17:22:45 UTC
HMDB IDHMDB0133489
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
Description2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid, also known as vanilmandelic acid or 3-methoxy-4-hydroxymandelic acid, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid exists in all living organisms, ranging from bacteria to humans. An aromatic ether that is the 3-O-methyl ether of 3,4-dihydroxymandelic acid.
Structure
Data?1563876068
Synonyms
ValueSource
3-Methoxy-4-hydroxymandelic acidChEBI
Hydroxy(4-hydroxy-3-methoxyphenyl)acetic acidChEBI
Vanilmandelic acidChEBI
Vanillylmandelic acidKegg
3-Methoxy-4-hydroxymandelateGenerator
Hydroxy(4-hydroxy-3-methoxyphenyl)acetateGenerator
VanilmandelateGenerator
VanillylmandelateGenerator
2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetateGenerator
Acid, 4-hydroxy-3-methoxymandelicHMDB
Acid, methoxyhydroxymandelicHMDB
Acid, vanillylmandelicHMDB
Acid, vanilmandelicHMDB
Methoxyhydroxymandelic acidHMDB
4 Hydroxy 3 methoxymandelic acidHMDB
4-Hydroxy-3-methoxymandelic acidHMDB
Chemical FormulaC9H10O5
Average Molecular Weight198.1727
Monoisotopic Molecular Weight198.05282343
IUPAC Name2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
Traditional Namevanillylmandelic acid
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(=C1)C(O)C(O)=O
InChI Identifier
InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)
InChI KeyCGQCWMIAEPEHNQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

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
logP0.94ALOGPS
logP0.43ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.15 m³·mol⁻¹ChemAxon
Polarizability18.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0002-1491000000-7f5d648c672e16020470Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-009t-7396100000-b5450c24921a68f5f6b3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3900000000-97b85fd5a9736a5d5eb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f7k-0900000000-0767bb6b6e228e056968Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-19fb61f26dd1382803c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmr-3900000000-447b05ffefbd29558da8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-b489fe6bd4be10b39c4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ukj-0900000000-8287953608f65abe096fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-4900000000-5d0f657dbcaa907fc20bSpectrum
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 IDFDB090532
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05584
BioCyc IDVANILLYL_MANDELATE
BiGG IDNot Available
Wikipedia LinkVanillylmandelic_acid
METLIN IDNot Available
PubChem Compound1245
PDB IDNot Available
ChEBI ID20106
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.