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Record Information
Version3.6
Creation Date2013-06-18 17:42:30 UTC
Update Date2017-03-02 22:05:17 UTC
HMDB IDHMDB60655
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxylidocaine
Description3-Hydroxylidocaine 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 FormulaC14H22N2O2
Average Molecular Weight250.3367
Monoisotopic Molecular Weight250.168127958
IUPAC Name2-(diethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide
Traditional Name2-(diethylamino)-N-(3-hydroxy-2,6-dimethylphenyl)acetamide
CAS Registry NumberNot Available
SMILES
CCN(CC)CC(=O)NC1=C(C)C=CC(O)=C1C
InChI Identifier
InChI=1S/C14H22N2O2/c1-5-16(6-2)9-13(18)15-14-10(3)7-8-12(17)11(14)4/h7-8,17H,5-6,9H2,1-4H3,(H,15,18)
InChI KeyPMGUCIDDSCRAMY-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
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen compound
  • 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 Solubility1.3 mg/mLALOGPS
logP1.69ALOGPS
logP2.54ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.04ChemAxon
pKa (Strongest Basic)7.73ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.57 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity75.91 m3·mol-1ChemAxon
Polarizability28.69 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 IDDBMET00256
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16560
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB60655
      Metagene LinkHMDB60655
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available