Showing Compound Card for Methyl anthranilate (CDB000635)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 25 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:47:52 UTC
Updated at2020-12-07 19:07:36 UTC
CannabisDB IDCDB000635
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMethyl anthranilate
DescriptionMethyl anthranilate or Methyl 2-aminobenzoate, also known as 2-carbomethoxyaniline, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Methyl anthranilate is a moderately basic compound (based on its pKa). It has a fruity grape smell, and one of its key uses is as a flavoring agent. Methyl 2-aminobenzoate is a bitter, flower, and fruity tasting compound. Methyl 2-aminobenzoate has been detected, but not quantified, in several different foods, such as tea, fruits, limes. Methyl anthranilate is known to occur naturally in the Concord grapes and other Vitis labrusca grapes and hybrids thereof. It has also been detected in bergamot, black locust, champak, gardenia, jasmine, lemon, mandarin orange, neroli, oranges, rue oil, strawberry, tuberose, wisteria, galangal, and ylang ylang. It is also a primary component of the essential apple flavor, along with ethyl acetate and ethyl butyrate. Methyl anthranilate is used extensively in modern perfumery. Methyl anthranilate has been reported to be a volatile component in cannabis samples (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(Methoxycarbonyl)anilineChEBI
2-Aminobenzoic acid methyl esterChEBI
2-CarbomethoxyanilineChEBI
Anthranilic acid methyl esterChEBI
Methyl O-aminobenzoateChEBI
O-Aminobenzoic acid methyl esterChEBI
O-CarbomethoxyanilineChEBI
O-Methyl anthranilateChEBI
2-Aminobenzoate methyl esterGenerator
Anthranilate methyl esterGenerator
Methyl O-aminobenzoic acidGenerator
O-Aminobenzoate methyl esterGenerator
O-Methyl anthranilic acidGenerator
Methyl 2-aminobenzoic acidGenerator
CarbomethoxyanilineHMDB
FEMA 2682HMDB
Methyl ester OF O-aminobenzoic acidHMDB
O-amino Methyl benzoateHMDB
Methyl anthranilic acidGenerator
Chemical FormulaC8H9NO2
Average Molecular Weight151.16
Monoisotopic Molecular Weight151.0633
IUPAC Namemethyl 2-aminobenzoate
Traditional Namemethyl anthranilate
CAS Registry Number134-20-3
SMILES
COC(=O)C1=CC=CC=C1N
InChI Identifier
InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
InChI KeyVAMXMNNIEUEQDV-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
  • Vinylogous amide
  • Methyl ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • 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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point24 - 25 °CNot Available
Boiling Point256 °CWikipedia
Water Solubility2.85 mg/mL at 25 °CNot Available
logP1.88Not Available
Predicted Properties
PropertyValueSource
logP1.6ALOGPS
logP1.8ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)19.4ChemAxon
pKa (Strongest Basic)2.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.78 m³·mol⁻¹ChemAxon
Polarizability15.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSMethyl anthranilate, non-derivatized, GC-MS Spectrumsplash10-014l-9700000000-dfe3727f600ad4c1a3fcSpectrum
GC-MSMethyl anthranilate, non-derivatized, GC-MS Spectrumsplash10-0gb9-4900000000-aadfdb770e0e737f8b6aSpectrum
GC-MSMethyl anthranilate, non-derivatized, GC-MS Spectrumsplash10-014l-9700000000-dfe3727f600ad4c1a3fcSpectrum
GC-MSMethyl anthranilate, non-derivatized, GC-MS Spectrumsplash10-0gb9-4900000000-aadfdb770e0e737f8b6aSpectrum
Predicted GC-MSMethyl anthranilate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6900000000-cbb0e5d181285b3afaaaSpectrum
Predicted GC-MSMethyl anthranilate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-00di-0900000000-47d3bade84c5e4931d1c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-00di-0900000000-185dd522a1fc548b72b82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-00di-2900000000-edbf763056e8c72de0312020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-00di-3900000000-80e68c81bbbd6961e0562020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-00dl-7900000000-f4d89a4912bba552a83c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-006x-9500000000-4073b13420f4b0056e902020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-00r6-9300000000-c45c4c69c1883e3f44ee2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-00kf-9100000000-d3ce7a6d45c89cf32c042020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-014l-9000000000-c093597fba151c4609c72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-014l-9000000000-6de4e61444f60c359ad82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-014i-9000000000-0fd51fb715e0e72a65d32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-014i-9000000000-b2a65db09df351a67eca2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-014i-9000000000-597af6cb6895ca4458302020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-00di-0900000000-6b7e5480efd4530cb4762020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-00di-0900000000-653b9ca77b6a92b0559b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-00di-0900000000-3b4c970d594e7e84da2f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0udi-0900000000-472f1d1c5d63a30785c42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0udi-0900000000-e5870501e95fd449a7bd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0uk9-0900000000-dcb6e65cc8cfb2f974ca2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-8f28628545d92d6eba852016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-2900000000-2eab000fe93ae5bfde362016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi3-9100000000-56145c723f7acb283fee2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-53f5c61d1ffff7e9c43e2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-5ddd8e2bdd8ab9a9f5f92016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9700000000-5b947aa002295f2ebfae2016-08-04View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 2 member 10TAS2R1012p13Q9NYW0 details
Taste receptor type 2 member 16TAS2R167q31.1-q31.3|7q31Q9NYV7 details
Taste receptor type 2 member 40TAS2R407q34P59535 details
Taste receptor type 2 member 3TAS2R37q31.3-q32Q9NYW6 details
Taste receptor type 2 member 4TAS2R47q31.3-q32Q9NYW5 details
Taste receptor type 2 member 7TAS2R712p13Q9NYW3 details
Taste receptor type 2 member 9TAS2R912p13Q9NYW1 details
Taste receptor type 2 member 50TAS2R5012p13.2P59544 details
Taste receptor type 2 member 38TAS2R387q34P59533 details
Taste receptor type 2 member 31TAS2R3112p13.2P59538 details
Taste receptor type 2 member 1TAS2R15p15.31Q9NYW7 details
Taste receptor type 2 member 20TAS2R2012p13.2P59543 details
Taste receptor type 2 member 39TAS2R397q34P59534 details
Taste receptor type 2 member 19TAS2R1912p13.2P59542 details
Taste receptor type 2 member 45TAS2R45P59539 details
Taste receptor type 2 member 30TAS2R3012p13.2P59541 details
Taste receptor type 2 member 42TAS2R42Q7RTR8 details
Taste receptor type 2 member 41TAS2R417q35P59536 details
Taste receptor type 2 member 43TAS2R4312p13.2P59537 details
Taste receptor type 2 member 5TAS2R57q34Q9NYW4 details
Taste receptor type 2 member 46TAS2R4612p13.2P59540 details
Taste receptor type 2 member 13TAS2R1312p13.2Q9NYV9 details
Taste receptor type 2 member 60TAS2R607q35P59551 details
Taste receptor type 2 member 8TAS2R812p13.2Q9NYW2 details
Taste receptor type 2 member 14TAS2R1412p13.2Q9NYV8 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029703
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000897
KNApSAcK IDC00034600
Chemspider ID13858096
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl_anthranilate
METLIN IDNot Available
PubChem Compound8635
PDB IDNot Available
ChEBI ID73244
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Only showing the first 10 proteins. There are 25 proteins in total.

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Only showing the first 10 proteins. There are 25 proteins in total.

Show All