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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-18 17:42:33 UTC
Update Date2017-10-23 19:15:45 UTC
HMDB IDHMDB0060656
Secondary Accession Numbers
  • HMDB60656
Metabolite Identification
Common NameMonoethylglycinexylidide
DescriptionMonoethylglycinexylidide 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
2-ethylamino-2',6'-AcetoxylidideChEBI
2-ethylamino-2,6-AcetoxylidineChEBI
EthylglycylxylidideChEBI
Lidocaine N-de-ethylated metaboliteChEBI
N-(2,6-Dimethylphenyl)-2-(ethylamino)acetamideChEBI
N-EthylglycinexylidideChEBI
NorlidocaineChEBI
Omega-(ethylamino)-2',6'-dimethylacetanilideChEBI
MEGXMeSH
Monoethylglycinexylidide, 3H,1-(14)C-labeledMeSH
Monoethylglycinexylidide monohydrochlorideMeSH
Chemical FormulaC12H18N2O
Average Molecular Weight206.2841
Monoisotopic Molecular Weight206.141913208
IUPAC NameN-(2,6-dimethylphenyl)-2-(ethylamino)acetamide
Traditional Namemonoethylglycinexylidide
CAS Registry NumberNot Available
SMILES
CCNCC(=O)NC1=C(C)C=CC=C1C
InChI Identifier
InChI=1S/C12H18N2O/c1-4-13-8-11(15)14-12-9(2)6-5-7-10(12)3/h5-7,13H,4,8H2,1-3H3,(H,14,15)
InChI KeyWRMRXPASUROZGT-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
  • Anilide
  • N-arylamide
  • M-xylene
  • Xylene
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary amine
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  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 Solubility0.42 g/LALOGPS
logP1.42ALOGPS
logP2.1ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)13.79ChemAxon
pKa (Strongest Basic)8.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.89 m³·mol⁻¹ChemAxon
Polarizability24 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, Positivesplash10-0ab9-9700000000-59871f7e43874a6af753View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9030000000-b30eeaf4741641f18682View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-7bcf920a7c1f71061bd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-67742f48ee8088bdd523View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0290000000-01db66bd1dc1702ff20aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-5980000000-47d25e48c36e75d3740cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-4900000000-26847048db306bbbfda5View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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
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 IDDBMET00257
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16561
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI ID222828
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available