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Record Information
Version4.0
Creation Date2013-06-18 18:42:46 UTC
Update Date2017-09-27 08:43:52 UTC
HMDB IDHMDB0060678
Secondary Accession Numbers
  • HMDB60678
Metabolite Identification
Common Name3-Hydroxymonoethylglycinexylidide
Description3-Hydroxymonoethylglycinexylidide is a metabolite of lidocaine. Lidocaine, Xylocaine, or lignocaine is a common local anesthetic and antiarrhythmic drug. Lidocaine is used topically to relieve itching, burning and pain from skin inflammations, injected as a dental anesthetic or as a local anesthetic for minor surgery. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
3-OH-MEGXMeSH
3-Hydroxy-monoethylglycinexylidideMeSH
N-(3-Hydroxy-2,6-dimethylphenyl)-2-ethylaminoacetamideMeSH
Chemical FormulaC12H18N2O2
Average Molecular Weight222.2835
Monoisotopic Molecular Weight222.13682783
IUPAC Name2-(ethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide
Traditional Name2-(ethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide
CAS Registry NumberNot Available
SMILES
CCNCC(=O)NC1=C(C)C=CC(O)=C1C
InChI Identifier
InChI=1S/C12H18N2O2/c1-4-13-7-11(16)14-12-8(2)5-6-10(15)9(12)3/h5-6,13,15H,4,7H2,1-3H3,(H,14,16)
InChI KeyYITCMQBVWIHTTA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • Xylenol
  • Anilide
  • O-cresol
  • P-cresol
  • M-xylene
  • Xylene
  • N-arylamide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary aliphatic amine
  • Secondary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility0.41 g/LALOGPS
logP1.04ALOGPS
logP1.63ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)10.05ChemAxon
pKa (Strongest Basic)8.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.36 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.87 m³·mol⁻¹ChemAxon
Polarizability24.66 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9600000000-5f020072a97c73daae81View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9250000000-7456b076121b4fef0dd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9020000000-2b9c10fde02d305c23e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-6cbb699e2f4e53b0bd3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-fde7f5554300c141691eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-be80b1566ce55291a2bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00du-3950000000-727d3f372178fd4f618fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-8900000000-ede2452452b422be3133View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Lidocaine (Antiarrhythmic) PathwayPw000381Pw000381 greyscalePw000381 simpleNot Available
Lidocaine (Local Anaesthetic) Metabolism PathwayPw000596Pw000596 greyscalePw000596 simpleNot Available
Lidocaine (Local Anaesthetic) PathwayPw000404Pw000404 greyscalePw000404 simpleNot Available
Displaying all 3 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16572
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound3015693
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available