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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:57:47 UTC
Update Date2021-10-13 06:39:16 UTC
HMDB IDHMDB0034169
Secondary Accession Numbers
  • HMDB34169
Metabolite Identification
Common NameMethyl N-methylanthranilate
DescriptionMethyl N-methylanthranilate, also known as methyl methanthranilate or methyl N-methyl anthranylic acid, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Methyl N-methylanthranilate is a sweet, blossom, and fruity tasting compound. Methyl N-methylanthranilate has been detected, but not quantified in, a few different foods, such as citrus, mandarin orange (clementine, tangerine), and sweet oranges (Citrus sinensis). This could make methyl N-methylanthranilate a potential biomarker for the consumption of these foods. Methyl N-methylanthranilate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Methyl N-methylanthranilate.
Structure
Data?1563862521
Synonyms
ValueSource
2-Methylaminobenzoic acid methyl esterChEBI
2-Methylaminomethyl benzoateChEBI
Dimethyl anthranilateChEBI
Methyl methanthranilateChEBI
Methyl methylaminobenzoateChEBI
Methyl methylanthranilateChEBI
Methyl N-methyl anthranylateChEBI
N-Methylanthranilic acid, methyl esterChEBI
2-Methylaminobenzoate methyl esterGenerator
2-Methylaminomethyl benzoic acidGenerator
Dimethyl anthranilic acidGenerator
Methyl methanthranilic acidGenerator
Methyl methylaminobenzoic acidGenerator
Methyl methylanthranilic acidGenerator
Methyl N-methyl anthranylic acidGenerator
N-Methylanthranilate, methyl esterGenerator
Methyl N-methylanthranilic acidGenerator
2-methylamino-Benzoic acid methyl esterHMDB
Anthranilic acid, N-methyl-, methyl esterHMDB
Benzoic acid, 2-(methylamino)-, methyl esterHMDB
FEMA 2718HMDB
Methyl 2-(methylamino)benzoateHMDB
Methyl 2-methylaminobenzoateHMDB
Methyl benzoate, 2-methylaminoHMDB
Methyl N-methyl anthranilateHMDB
Methyl N-methyl-O-anthranilateHMDB
Methyl O-(methylamino)benzoateHMDB
Methyl-2-(N-methylamino)benzoateHMDB
Methyl-N-methylanthranilateHMDB
N-Methyl methyl anthranilateHMDB
Methyl 2-(methylamino)benzoic acidGenerator
Methyl N-methylanthranilateMeSH
Chemical FormulaC9H11NO2
Average Molecular Weight165.1891
Monoisotopic Molecular Weight165.078978601
IUPAC Namemethyl 2-(methylamino)benzoate
Traditional Namemethyl 2-(methylamino)benzoate
CAS Registry Number85-91-6
SMILES
CNC1=CC=CC=C1C(=O)OC
InChI Identifier
InChI=1S/C9H11NO2/c1-10-8-6-4-3-5-7(8)9(11)12-2/h3-6,10H,1-2H3
InChI KeyGVOWHGSUZUUUDR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Aminobenzoic acid or derivatives
  • Benzoate ester
  • Benzoyl
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Secondary aliphatic/aromatic amine
  • Vinylogous amide
  • Methyl ester
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point19 °CNot Available
Boiling Point255.00 to 256.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility475 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP2.531 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.69 g/LALOGPS
logP10(1.75) g/LALOGPS
logP10(2.1) g/LChemAxon
logS10(-1.8) g/LALOGPS
pKa (Strongest Acidic)19.59ChemAxon
pKa (Strongest Basic)2.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.28 m³·mol⁻¹ChemAxon
Polarizability17.6 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.94331661259
DarkChem[M-H]-134.42131661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methyl N-methylanthranilate GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-3900000000-71dd24a94747bc71cff42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl N-methylanthranilate 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 - Methyl N-methylanthranilate 10V, Positive-QTOFsplash10-014i-0900000000-af87edaa1391f623356d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 20V, Positive-QTOFsplash10-0159-0900000000-b7d3f91cccbccb6109a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 40V, Positive-QTOFsplash10-0pc0-8900000000-7900a388e2a9753b49c42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 10V, Negative-QTOFsplash10-03di-0900000000-f0fe7fc3060819b5a0a22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 20V, Negative-QTOFsplash10-03di-0900000000-5e8fda07dbb8dc499d1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 40V, Negative-QTOFsplash10-0ue9-4900000000-15fa8f5d7c70fff9299d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 10V, Positive-QTOFsplash10-001i-0900000000-409c0f325aa5ec0f6a9f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 20V, Positive-QTOFsplash10-001i-0900000000-4b51ded70599867568332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 40V, Positive-QTOFsplash10-0ldi-9200000000-1b920371adb5ce1a24fc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 10V, Negative-QTOFsplash10-03di-0900000000-a7afb973c05f34cd28a72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 20V, Negative-QTOFsplash10-0a4i-0900000000-4c001580e59aedfbd58c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 40V, Negative-QTOFsplash10-0ik9-7900000000-0fe6bf21e9c43f76d2422021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H 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 IDFDB012455
KNApSAcK IDNot Available
Chemspider ID21108245
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6826
PDB IDNot Available
ChEBI ID142267
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1004392
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.. .