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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 18:42:50 UTC
Update Date2019-07-23 07:14:50 UTC
HMDB IDHMDB0060679
Secondary Accession Numbers
  • HMDB60679
Metabolite Identification
Common NameGlycinexylidide
DescriptionGlycinexylidide, also known as GX, belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions. 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. Glycinexylidide is a metabolite of lidocaine. Glycinexylidide is a very strong basic compound (based on its pKa). In humans, glycinexylidide is involved in lidocaine (local anaesthetic) metabolism pathway. Lidocaine, Xylocaine, or lignocaine is a common local anesthetic and antiarrhythmic drug.
Structure
Data?1563866090
Synonyms
ValueSource
2-Amino-2',6'-acetoxylidideChEBI
2-Amino-2',6'-dimethylacetoanilideChEBI
2-Amino-N-(2,6-dimethyl-phenyl)-acetamideChEBI
Glycine xylidideChEBI
GlycylxylidideChEBI
GXChEBI
N-(2,6-Dimethylphenyl)-2-aminoacetamideChEBI
N-(2,6-Dimethylphenyl)glycinamideChEBI
Glycinexylidide monohydrochlorideHMDB
Chemical FormulaC10H14N2O
Average Molecular Weight178.231
Monoisotopic Molecular Weight178.11061308
IUPAC Name2-amino-N-(2,6-dimethylphenyl)acetamide
Traditional Nameglycinexylidide
CAS Registry NumberNot Available
SMILES
CC1=CC=CC(C)=C1NC(=O)CN
InChI Identifier
InChI=1S/C10H14N2O/c1-7-4-3-5-8(2)10(7)12-9(13)6-11/h3-5H,6,11H2,1-2H3,(H,12,13)
InChI KeyIXYVBZOSGGJWCW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassXylenes
Direct Parentm-Xylenes
Alternative Parents
Substituents
  • M-xylene
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • 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 Solubility1.11 g/LALOGPS
logP10(0.18) g/LALOGPS
logP10(1.31) g/LChemAxon
logS10(-2.2) g/LALOGPS
pKa (Strongest Acidic)13.79ChemAxon
pKa (Strongest Basic)7.98ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.36 m³·mol⁻¹ChemAxon
Polarizability19.73 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]+140.80331661259
DarkChem[M-H]-137.03431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GlycinexylidideCC1=CC=CC(C)=C1NC(=O)CN2482.3Standard polar33892256
GlycinexylidideCC1=CC=CC(C)=C1NC(=O)CN1690.2Standard non polar33892256
GlycinexylidideCC1=CC=CC(C)=C1NC(=O)CN1747.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glycinexylidide,1TMS,isomer #1CC1=CC=CC(C)=C1NC(=O)CN[Si](C)(C)C1828.4Semi standard non polar33892256
Glycinexylidide,1TMS,isomer #1CC1=CC=CC(C)=C1NC(=O)CN[Si](C)(C)C1740.3Standard non polar33892256
Glycinexylidide,1TMS,isomer #1CC1=CC=CC(C)=C1NC(=O)CN[Si](C)(C)C2437.9Standard polar33892256
Glycinexylidide,1TMS,isomer #2CC1=CC=CC(C)=C1N(C(=O)CN)[Si](C)(C)C1643.4Semi standard non polar33892256
Glycinexylidide,1TMS,isomer #2CC1=CC=CC(C)=C1N(C(=O)CN)[Si](C)(C)C1739.9Standard non polar33892256
Glycinexylidide,1TMS,isomer #2CC1=CC=CC(C)=C1N(C(=O)CN)[Si](C)(C)C2438.1Standard polar33892256
Glycinexylidide,2TMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C1747.8Semi standard non polar33892256
Glycinexylidide,2TMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C1822.7Standard non polar33892256
Glycinexylidide,2TMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C2078.4Standard polar33892256
Glycinexylidide,2TMS,isomer #2CC1=CC=CC(C)=C1NC(=O)CN([Si](C)(C)C)[Si](C)(C)C1984.3Semi standard non polar33892256
Glycinexylidide,2TMS,isomer #2CC1=CC=CC(C)=C1NC(=O)CN([Si](C)(C)C)[Si](C)(C)C1921.3Standard non polar33892256
Glycinexylidide,2TMS,isomer #2CC1=CC=CC(C)=C1NC(=O)CN([Si](C)(C)C)[Si](C)(C)C2336.7Standard polar33892256
Glycinexylidide,3TMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1903.5Semi standard non polar33892256
Glycinexylidide,3TMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1970.0Standard non polar33892256
Glycinexylidide,3TMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2043.3Standard polar33892256
Glycinexylidide,1TBDMS,isomer #1CC1=CC=CC(C)=C1NC(=O)CN[Si](C)(C)C(C)(C)C2064.3Semi standard non polar33892256
Glycinexylidide,1TBDMS,isomer #1CC1=CC=CC(C)=C1NC(=O)CN[Si](C)(C)C(C)(C)C1964.2Standard non polar33892256
Glycinexylidide,1TBDMS,isomer #1CC1=CC=CC(C)=C1NC(=O)CN[Si](C)(C)C(C)(C)C2509.3Standard polar33892256
Glycinexylidide,1TBDMS,isomer #2CC1=CC=CC(C)=C1N(C(=O)CN)[Si](C)(C)C(C)(C)C1879.9Semi standard non polar33892256
Glycinexylidide,1TBDMS,isomer #2CC1=CC=CC(C)=C1N(C(=O)CN)[Si](C)(C)C(C)(C)C1929.1Standard non polar33892256
Glycinexylidide,1TBDMS,isomer #2CC1=CC=CC(C)=C1N(C(=O)CN)[Si](C)(C)C(C)(C)C2501.6Standard polar33892256
Glycinexylidide,2TBDMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2204.7Semi standard non polar33892256
Glycinexylidide,2TBDMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2230.1Standard non polar33892256
Glycinexylidide,2TBDMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2325.5Standard polar33892256
Glycinexylidide,2TBDMS,isomer #2CC1=CC=CC(C)=C1NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2422.2Semi standard non polar33892256
Glycinexylidide,2TBDMS,isomer #2CC1=CC=CC(C)=C1NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2288.2Standard non polar33892256
Glycinexylidide,2TBDMS,isomer #2CC1=CC=CC(C)=C1NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2490.5Standard polar33892256
Glycinexylidide,3TBDMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2590.0Semi standard non polar33892256
Glycinexylidide,3TBDMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2532.6Standard non polar33892256
Glycinexylidide,3TBDMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2399.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glycinexylidide GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9800000000-5805697b21d5e8be230a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycinexylidide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycinexylidide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 10V, Positive-QTOFsplash10-004i-4900000000-f007d2e6587e7eb5f04c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 20V, Positive-QTOFsplash10-053r-9500000000-b21f8610ff8b2bd683392017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 40V, Positive-QTOFsplash10-0a59-9400000000-30ac1821a4bfe83f47bf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 10V, Negative-QTOFsplash10-004i-0900000000-361255e779c1e47f749c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 20V, Negative-QTOFsplash10-00b9-0900000000-b3aa7081b0cca88833742017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 40V, Negative-QTOFsplash10-00di-2900000000-fec20460cbf1144235b22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 10V, Positive-QTOFsplash10-05di-0900000000-334892eb981d32eece132021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 20V, Positive-QTOFsplash10-074i-0900000000-86c4e42bacae35b08ba22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 40V, Positive-QTOFsplash10-0a4i-3900000000-f0327e19dfdbb241d3552021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 10V, Negative-QTOFsplash10-00fr-0900000000-a9d398a953f9e0b363d32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 20V, Negative-QTOFsplash10-00di-5900000000-40f955149c450c9140522021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycinexylidide 40V, Negative-QTOFsplash10-0fdo-6900000000-fa246a6254dba94fcd992021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDC16569
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound87833
PDB IDNot Available
ChEBI ID357241
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