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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 17:42:30 UTC
Update Date2019-07-23 07:14:47 UTC
HMDB IDHMDB0060655
Secondary Accession Numbers
  • HMDB60655
Metabolite Identification
Common Name3-Hydroxylidocaine
Description3-Hydroxylidocaine belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. 3-Hydroxylidocaine is a metabolite of lidocaine. 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. 3-Hydroxylidocaine is a very strong basic compound (based on its pKa). 3-hydroxylidocaine can be biosynthesized from lidocaine through the action of the enzymes cytochrome P450 1A2 and cytochrome P450 3A4. In humans, 3-hydroxylidocaine is involved in lidocaine (local anaesthetic) metabolism pathway. Lidocaine, Xylocaine, or lignocaine is a common local anesthetic and antiarrhythmic drug.
Structure
Data?1563866087
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
Description 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
  • 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
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.3 g/LALOGPS
logP10(1.69) g/LALOGPS
logP10(2.54) g/LChemAxon
logS10(-2.3) g/LALOGPS
pKa (Strongest Acidic)10.04ChemAxon
pKa (Strongest Basic)7.73ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.57 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity75.91 m³·mol⁻¹ChemAxon
Polarizability28.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.86131661259
DarkChem[M-H]-158.97331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-HydroxylidocaineCCN(CC)CC(=O)NC1=C(C)C=CC(O)=C1C2923.2Standard polar33892256
3-HydroxylidocaineCCN(CC)CC(=O)NC1=C(C)C=CC(O)=C1C2126.2Standard non polar33892256
3-HydroxylidocaineCCN(CC)CC(=O)NC1=C(C)C=CC(O)=C1C2172.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxylidocaine,1TMS,isomer #1CCN(CC)CC(=O)NC1=C(C)C=CC(O[Si](C)(C)C)=C1C2157.7Semi standard non polar33892256
3-Hydroxylidocaine,1TMS,isomer #2CCN(CC)CC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C1947.4Semi standard non polar33892256
3-Hydroxylidocaine,2TMS,isomer #1CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C1988.2Semi standard non polar33892256
3-Hydroxylidocaine,2TMS,isomer #1CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C2057.7Standard non polar33892256
3-Hydroxylidocaine,2TMS,isomer #1CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C)=C1C)[Si](C)(C)C2335.1Standard polar33892256
3-Hydroxylidocaine,1TBDMS,isomer #1CCN(CC)CC(=O)NC1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C2426.0Semi standard non polar33892256
3-Hydroxylidocaine,1TBDMS,isomer #2CCN(CC)CC(=O)N(C1=C(C)C=CC(O)=C1C)[Si](C)(C)C(C)(C)C2214.5Semi standard non polar33892256
3-Hydroxylidocaine,2TBDMS,isomer #1CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C2496.1Semi standard non polar33892256
3-Hydroxylidocaine,2TBDMS,isomer #1CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C2446.3Standard non polar33892256
3-Hydroxylidocaine,2TBDMS,isomer #1CCN(CC)CC(=O)N(C1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)[Si](C)(C)C(C)(C)C2593.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxylidocaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9610000000-7d9e7465a3e0b86f4e102017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxylidocaine GC-MS (1 TMS) - 70eV, Positivesplash10-0a4r-9241000000-6c2fc67a46d746d33c942017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxylidocaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxylidocaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 20V, Positive-QTOFsplash10-000i-9000000000-4041439bd0fd4cf8d7902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Positive-QTOFsplash10-0f79-9050000000-fd33f5e9645eebea97b32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Positive-QTOFsplash10-0udr-7090000000-e12b82694dc9a32cacc92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 30V, Positive-QTOFsplash10-000i-9000000000-ed4771fea10716df5db52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Positive-QTOFsplash10-0udr-7090000000-8c5bac2e6e0519905c1b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 0V, Positive-QTOFsplash10-0udi-0090000000-8570de4f92c1821694992021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 30V, Positive-QTOFsplash10-000i-9000000000-bd37225fee133191cf612021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 0V, Positive-QTOFsplash10-0udi-0090000000-ed309985d4bd9c39233e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 40V, Negative-QTOFsplash10-053i-2900000000-6477f8d10de3ae00fc3e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 30V, Negative-QTOFsplash10-000i-0900000000-77e96289ee434fe70d612021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Negative-QTOFsplash10-0002-0290000000-0c7cb9ce98125c219def2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 20V, Negative-QTOFsplash10-000i-0920000000-0852a8bcf3d408b828c32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 30V, Positive-QTOFsplash10-000i-9000000000-7560cc1a08f730a340c62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxylidocaine 40V, Positive-QTOFsplash10-000i-9000000000-1496edf216edbb2a3e792021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Positive-QTOFsplash10-000i-9010000000-ad5e26b784dac6c93a4c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 20V, Positive-QTOFsplash10-000i-9000000000-02759b67c995186ef23a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 40V, Positive-QTOFsplash10-0a4r-9000000000-da6bc9e6cf9a4198ce992017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Negative-QTOFsplash10-0002-0190000000-cdc94b355bef03bf44652017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 20V, Negative-QTOFsplash10-0072-2980000000-acaf3c5aea41c1d8ec7f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 40V, Negative-QTOFsplash10-059f-9800000000-ad581d0e4a1f210786892017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Positive-QTOFsplash10-0udi-1090000000-7dce5a6948f756fcfd542021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 20V, Positive-QTOFsplash10-000i-9610000000-16e94f02639a739b0e392021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 40V, Positive-QTOFsplash10-0a4r-9300000000-cc8630abd8a5e02e98972021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 10V, Negative-QTOFsplash10-000j-0980000000-b9615244ae6ddc09718f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxylidocaine 20V, Negative-QTOFsplash10-000i-2900000000-16a846300720890f70632021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16560
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound161824
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available