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Record Information
Version3.6
Creation Date2013-06-18 18:42:46 UTC
Update Date2016-02-11 08:10:57 UTC
HMDB IDHMDB60678
Secondary Accession NumbersNone
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
SynonymsNot Available
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 KeyInChIKey=YITCMQBVWIHTTA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • N-arylamide
  • P-cresol
  • O-cresol
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.87 m3·mol-1ChemAxon
Polarizability24.66 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB60678
Metagene LinkHMDB60678
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