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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:46 UTC
Update Date2022-03-07 02:53:24 UTC
HMDB IDHMDB0032609
Secondary Accession Numbers
  • HMDB32609
Metabolite Identification
Common Name2-(Methylamino)benzoic acid
Description2-(Methylamino)benzoic acid, also known as N-methylanthranilic acid or N-methyl-2-aminobenzoate, 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-(Methylamino)benzoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 2-(Methylamino)benzoic acid.
Structure
Data?1563862282
Synonyms
ValueSource
N-Methyl-2-aminobenzoic acidChEBI
N-Methyl-O-aminobenzoic acidChEBI
O-(Methylamino)benzoic acidChEBI
N-Methylanthranilic acidKegg
N-Methyl-2-aminobenzoateGenerator
N-Methyl-O-aminobenzoateGenerator
O-(Methylamino)benzoateGenerator
N-MethylanthranilateGenerator
2-(Methylamino)benzoateGenerator
2-(Methylamino)-benzoic acidHMDB
N-Methyl-anthranilic acidHMDB
N-Methylanthranilic acid, 8ciHMDB
2-(Methylamino)benzoic acidChEBI
Chemical FormulaC8H9NO2
Average Molecular Weight151.1626
Monoisotopic Molecular Weight151.063328537
IUPAC Name2-(methylamino)benzoic acid
Traditional NameN-methylanthranilic acid
CAS Registry Number119-68-6
SMILES
CNC1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C8H9NO2/c1-9-7-5-3-2-4-6(7)8(10)11/h2-5,9H,1H3,(H,10,11)
InChI KeyWVMBPWMAQDVZCM-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
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Secondary aliphatic/aromatic amine
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178 - 179 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available125.872http://allccs.zhulab.cn/database/detail?ID=AllCCS00000899
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.29 g/LALOGPS
logP1.12ALOGPS
logP1.75ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.85ChemAxon
pKa (Strongest Basic)1.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.51 m³·mol⁻¹ChemAxon
Polarizability15.4 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]+132.13331661259
DarkChem[M-H]-131.32331661259
DeepCCS[M+H]+130.82830932474
DeepCCS[M-H]-127.12130932474
DeepCCS[M-2H]-164.07130932474
DeepCCS[M+Na]+139.39130932474
AllCCS[M+H]+132.132859911
AllCCS[M+H-H2O]+127.532859911
AllCCS[M+NH4]+136.332859911
AllCCS[M+Na]+137.632859911
AllCCS[M-H]-128.532859911
AllCCS[M+Na-2H]-129.832859911
AllCCS[M+HCOO]-131.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-(Methylamino)benzoic acidCNC1=CC=CC=C1C(O)=O2529.0Standard polar33892256
2-(Methylamino)benzoic acidCNC1=CC=CC=C1C(O)=O1555.6Standard non polar33892256
2-(Methylamino)benzoic acidCNC1=CC=CC=C1C(O)=O1501.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-(Methylamino)benzoic acid,1TMS,isomer #1CNC1=CC=CC=C1C(=O)O[Si](C)(C)C1541.5Semi standard non polar33892256
2-(Methylamino)benzoic acid,1TMS,isomer #2CN(C1=CC=CC=C1C(=O)O)[Si](C)(C)C1613.3Semi standard non polar33892256
2-(Methylamino)benzoic acid,2TMS,isomer #1CN(C1=CC=CC=C1C(=O)O[Si](C)(C)C)[Si](C)(C)C1577.0Semi standard non polar33892256
2-(Methylamino)benzoic acid,2TMS,isomer #1CN(C1=CC=CC=C1C(=O)O[Si](C)(C)C)[Si](C)(C)C1668.7Standard non polar33892256
2-(Methylamino)benzoic acid,1TBDMS,isomer #1CNC1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C1796.1Semi standard non polar33892256
2-(Methylamino)benzoic acid,1TBDMS,isomer #2CN(C1=CC=CC=C1C(=O)O)[Si](C)(C)C(C)(C)C1836.9Semi standard non polar33892256
2-(Methylamino)benzoic acid,2TBDMS,isomer #1CN(C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2019.0Semi standard non polar33892256
2-(Methylamino)benzoic acid,2TBDMS,isomer #1CN(C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2051.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-(Methylamino)benzoic acid GC-EI-TOF (Non-derivatized)splash10-0a59-0910000000-9d3955d36691685069ff2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-(Methylamino)benzoic acid GC-EI-TOF (Non-derivatized)splash10-0a59-0910000000-9d3955d36691685069ff2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-(Methylamino)benzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zgi-3900000000-d25c1dc1732d530309312017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-(Methylamino)benzoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9430000000-496bdcb2263befa222eb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-(Methylamino)benzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-(Methylamino)benzoic acid 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 - 2-(Methylamino)benzoic acid LC-ESI-QQ , negative-QTOFsplash10-0udi-0900000000-5955a4952e458a658cbe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid LC-ESI-QQ , negative-QTOFsplash10-0zfr-0900000000-49014cd27d32997916d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-2900000000-685e7b06c396ca5bc0722017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid LC-ESI-QQ , negative-QTOFsplash10-056u-9000000000-8b5c78380a5f0b31f6202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-b27641d2926e1d3e69ed2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid LC-ESI-QQ , positive-QTOFsplash10-000i-0900000000-58f0b9bf6b644da4e99a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid LC-ESI-QQ , positive-QTOFsplash10-00di-9200000000-4af52e4cba799817b3ca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid LC-ESI-QQ , positive-QTOFsplash10-0592-9200000000-3684f6153677daea6c032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid LC-ESI-QQ , positive-QTOFsplash10-002f-9000000000-3fd6fff4fa77ebb115062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid LC-ESI-QQ , positive-QTOFsplash10-004j-9000000000-3eeab274e028bdf635522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 35V, Negative-QTOFsplash10-0pb9-0900000000-d550021750fb8c0e72c82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 40V, Positive-QTOFsplash10-066r-0900000000-740c3b1947a395c8fbd62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 20V, Positive-QTOFsplash10-05o0-0900000000-2972138fe87fa2f4cbcd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 35V, Positive-QTOFsplash10-05q9-4900000000-13fd7d0b1e0616dfd6ed2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 10V, Positive-QTOFsplash10-001i-0900000000-813a31770d4502ff952e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 10V, Positive-QTOFsplash10-0udi-0900000000-e13d8c5a77a331248c802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 20V, Positive-QTOFsplash10-0pc0-0900000000-54a4b90bb965b6a8ab2d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 40V, Positive-QTOFsplash10-0zfr-9500000000-cb87c71a0f70e96f06512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 10V, Negative-QTOFsplash10-0pb9-0900000000-9b7b467ff3e8a333c43f2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 20V, Negative-QTOFsplash10-0a4i-1900000000-da98b296184a308e0a4e2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 40V, Negative-QTOFsplash10-052f-9500000000-8447a5153a144d1e86f52016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 10V, Negative-QTOFsplash10-0udi-0900000000-a85f926cb85cdd37a7472021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 20V, Negative-QTOFsplash10-0a4i-1900000000-b1aa1ec56d95d71aa6d72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 40V, Negative-QTOFsplash10-0kdi-9800000000-e65c0f81e56d6aafe0e22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-(Methylamino)benzoic acid 10V, Positive-QTOFsplash10-001i-0900000000-3cdac39ce46246bdfe3c2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010550
KNApSAcK IDNot Available
Chemspider ID60420
KEGG Compound IDC03005
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound67069
PDB IDNot Available
ChEBI ID16394
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1267231
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .