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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 18:49:44 UTC
Update Date2019-07-23 07:14:51 UTC
HMDB IDHMDB0060680
Secondary Accession Numbers
  • HMDB60680
Metabolite Identification
Common Name2-Amino-3-methylbenzoate
Description2-Amino-3-methylbenzoate belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. 2-Amino-3-methylbenzoate 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. 2-Amino-3-methylbenzoate is a moderately basic compound (based on its pKa). In humans, 2-amino-3-methylbenzoate is involved in lidocaine (local anaesthetic) metabolism pathway. Lidocaine, Xylocaine, or lignocaine is a common local anesthetic and antiarrhythmic drug.
Structure
Data?1563866091
Synonyms
ValueSource
2-Amino-3-methylbenzoic acidGenerator
2-Amino-3-methylbenzoic acid, monopotassium saltHMDB
Chemical FormulaC8H9NO2
Average Molecular Weight151.1626
Monoisotopic Molecular Weight151.063328537
IUPAC Name2-amino-3-methylbenzoic acid
Traditional Name2-amino-3-methylbenzoic acid
CAS Registry NumberNot Available
SMILES
CC1=C(N)C(=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C8H9NO2/c1-5-3-2-4-6(7(5)9)8(10)11/h2-4H,9H2,1H3,(H,10,11)
InChI KeyWNAJXPYVTFYEST-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Aminotoluene
  • Aniline or substituted anilines
  • Toluene
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen 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 Solubility2.94 g/LALOGPS
logP10(1.17) g/LALOGPS
logP10(1.97) g/LChemAxon
logS10(-1.7) g/LALOGPS
pKa (Strongest Acidic)4.87ChemAxon
pKa (Strongest Basic)1.88ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability15.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.68431661259
DarkChem[M-H]-127.41431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Amino-3-methylbenzoateCC1=C(N)C(=CC=C1)C(O)=O2931.7Standard polar33892256
2-Amino-3-methylbenzoateCC1=C(N)C(=CC=C1)C(O)=O1471.2Standard non polar33892256
2-Amino-3-methylbenzoateCC1=C(N)C(=CC=C1)C(O)=O1564.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Amino-3-methylbenzoate,1TMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N1542.8Semi standard non polar33892256
2-Amino-3-methylbenzoate,1TMS,isomer #2CC1=CC=CC(C(=O)O)=C1N[Si](C)(C)C1667.8Semi standard non polar33892256
2-Amino-3-methylbenzoate,2TMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N[Si](C)(C)C1679.1Semi standard non polar33892256
2-Amino-3-methylbenzoate,2TMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N[Si](C)(C)C1681.4Standard non polar33892256
2-Amino-3-methylbenzoate,2TMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N[Si](C)(C)C1862.0Standard polar33892256
2-Amino-3-methylbenzoate,2TMS,isomer #2CC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C)[Si](C)(C)C1696.3Semi standard non polar33892256
2-Amino-3-methylbenzoate,2TMS,isomer #2CC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C)[Si](C)(C)C1797.2Standard non polar33892256
2-Amino-3-methylbenzoate,2TMS,isomer #2CC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C)[Si](C)(C)C1889.9Standard polar33892256
2-Amino-3-methylbenzoate,3TMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C1677.9Semi standard non polar33892256
2-Amino-3-methylbenzoate,3TMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C1795.9Standard non polar33892256
2-Amino-3-methylbenzoate,3TMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C1769.8Standard polar33892256
2-Amino-3-methylbenzoate,1TBDMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N1812.5Semi standard non polar33892256
2-Amino-3-methylbenzoate,1TBDMS,isomer #2CC1=CC=CC(C(=O)O)=C1N[Si](C)(C)C(C)(C)C1921.2Semi standard non polar33892256
2-Amino-3-methylbenzoate,2TBDMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N[Si](C)(C)C(C)(C)C2142.6Semi standard non polar33892256
2-Amino-3-methylbenzoate,2TBDMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N[Si](C)(C)C(C)(C)C2063.2Standard non polar33892256
2-Amino-3-methylbenzoate,2TBDMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N[Si](C)(C)C(C)(C)C2151.9Standard polar33892256
2-Amino-3-methylbenzoate,2TBDMS,isomer #2CC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2150.2Semi standard non polar33892256
2-Amino-3-methylbenzoate,2TBDMS,isomer #2CC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2170.4Standard non polar33892256
2-Amino-3-methylbenzoate,2TBDMS,isomer #2CC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2118.6Standard polar33892256
2-Amino-3-methylbenzoate,3TBDMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2365.3Semi standard non polar33892256
2-Amino-3-methylbenzoate,3TBDMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2346.5Standard non polar33892256
2-Amino-3-methylbenzoate,3TBDMS,isomer #1CC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2174.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-methylbenzoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zgi-2900000000-850bf9aebbdb2215625a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-methylbenzoate GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9430000000-444c97d9fdf9de5523c72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Amino-3-methylbenzoate 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 - 2-Amino-3-methylbenzoate 10V, Positive-QTOFsplash10-0f8i-0900000000-6aa89ff37c1963b764f22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-methylbenzoate 20V, Positive-QTOFsplash10-053r-0900000000-d5c760bf6e946dce93342017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-methylbenzoate 40V, Positive-QTOFsplash10-00mx-9200000000-8d2b903d9723d9ab08d22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-methylbenzoate 10V, Negative-QTOFsplash10-0pb9-0900000000-55ce4a590992fbc502bb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-methylbenzoate 20V, Negative-QTOFsplash10-0a4i-0900000000-5bf66656437913693d512017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-methylbenzoate 40V, Negative-QTOFsplash10-0a4i-1900000000-7e483eaf361150d1847e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-methylbenzoate 10V, Positive-QTOFsplash10-001i-0900000000-1c86afb083f69d3378b92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-methylbenzoate 20V, Positive-QTOFsplash10-053r-0900000000-5a25ee06196bd8e1e8612021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-methylbenzoate 40V, Positive-QTOFsplash10-0a6r-9400000000-f96eb846e269b1e11b3a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-methylbenzoate 10V, Negative-QTOFsplash10-0a4i-0900000000-95c37ad0f0f4fd79f7e22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-methylbenzoate 20V, Negative-QTOFsplash10-0a4i-0900000000-c4d0aae8972e54aa63d32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Amino-3-methylbenzoate 40V, Negative-QTOFsplash10-0a4i-3900000000-9f4d6d91e4f229266f962021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 IDC16571
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound78101
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