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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2013-04-09 21:20:33 UTC
Update Date2019-07-23 07:13:26 UTC
HMDB IDHMDB0060026
Secondary Accession Numbers
  • HMDB60026
Metabolite Identification
Common NameVanilloylglycine
DescriptionVanilloylglycine (CAS# 1212-04-0), also known as N-Vanilloylglycine, is a non-phenolic metabolite. In human studies, Vanilloylglycine has been detected in urines of individuals consuming cocoa powder dissolved in milk. (Pheno-Explorer)
Structure
Data?1563866006
Synonyms
ValueSource
2-[(4-Hydroxy-3-methoxybenzoyl)amino]acetic acidHMDB
3-Methoxy-4-hydroxyhippuric acidHMDB
Chemical FormulaC10H11NO5
Average Molecular Weight225.198
Monoisotopic Molecular Weight225.063722467
IUPAC Name2-{[hydroxy(4-hydroxy-3-methoxyphenyl)methylidene]amino}acetic acid
Traditional Name{[hydroxy(4-hydroxy-3-methoxyphenyl)methylidene]amino}acetic acid
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(=C1)C(O)=NCC(O)=O
InChI Identifier
InChI=1S/C10H11NO5/c1-16-8-4-6(2-3-7(8)12)10(15)11-5-9(13)14/h2-4,12H,5H2,1H3,(H,11,15)(H,13,14)
InChI KeyLOODYTDRRBLQNH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hippuric acids. These are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHippuric acids
Alternative Parents
Substituents
  • Hippuric acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Benzoyl
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

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
Water Solubility2.24 g/LALOGPS
logP0.74ALOGPS
logP0.75ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)1.37ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.35 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.08 m³·mol⁻¹ChemAxon
Polarizability21.53 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1910000000-bb66a7ca5718ab36a3c6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00b9-9026400000-fb5a1bad52a62ba59184JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-3490000000-a9300847707f92a0a074JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0un9-4920000000-be775c57516238d77dd6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fmi-9700000000-3bb12254284908339974JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-4f92f07a3a935f792f5aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1970000000-70968ac99b79604070ddJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9800000000-302c7f6e7555688d77c7JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030006
KNApSAcK IDNot Available
Chemspider ID2340857
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3083688
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J: Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal Chem. 2012 Aug 21;84(16):7263-71. doi: 10.1021/ac3017339. Epub 2012 Aug 2. [PubMed:22827565 ]