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Record Information
Version3.6
Creation Date2013-06-18 17:42:33 UTC
Update Date2017-03-02 22:05:18 UTC
HMDB IDHMDB60656
Secondary Accession NumbersNone
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
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.89 m3·mol-1ChemAxon
Polarizability24 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Lidocaine (Antiarrhythmic) PathwaySMP00328Not Available
Lidocaine (Local Anaesthetic) Metabolism PathwaySMP00620Not Available
Lidocaine (Local Anaesthetic) PathwaySMP00398Not 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
      NuGOwiki LinkHMDB60656
      Metagene LinkHMDB60656
      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