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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:57:47 UTC
Update Date2019-07-23 06:15:21 UTC
HMDB IDHMDB0034169
Secondary Accession Numbers
  • HMDB34169
Metabolite Identification
Common NameMethyl N-methylanthranilate
DescriptionMethyl N-methylanthranilate, also known as methyl methanthranilate or methyl methylaminobenzoate, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. A methyl ester resulting from the formal condensation of the carboxy group of N-methylanthranilic acid with methanol. Methyl N-methylanthranilate is a moderately basic compound (based on its pKa). Methyl N-methylanthranilate is a sweet, blossom, and fruity tasting compound. Outside of the human body, Methyl N-methylanthranilate has been detected, but not quantified in, a few different foods, such as citrus, mandarin orange (clementine, tangerine), and sweet oranges. This could make methyl N-methylanthranilate a potential biomarker for the consumption of these foods.
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point19 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.69 g/LALOGPS
logP1.75ALOGPS
logP2.1ChemAxon
logS-1.8ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-3900000000-71dd24a94747bc71cff4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-af87edaa1391f623356dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0900000000-b7d3f91cccbccb6109a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc0-8900000000-7900a388e2a9753b49c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-f0fe7fc3060819b5a0a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-5e8fda07dbb8dc499d1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-4900000000-15fa8f5d7c70fff9299dSpectrum
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
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.. .