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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:57:29 UTC
Update Date2023-02-21 17:25:56 UTC
HMDB IDHMDB0037697
Secondary Accession Numbers
  • HMDB37697
Metabolite Identification
Common NameIsobutyl N-methylanthranilate
DescriptionIsobutyl N-methylanthranilate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Isobutyl N-methylanthranilate is a fruity and grapefruit tasting compound. Based on a literature review very few articles have been published on Isobutyl N-methylanthranilate.
Structure
Data?1677000356
Synonyms
ValueSource
Isobutyl N-methylanthranilic acidGenerator
2-Methylpropyl 2-(methylamino)benzoateHMDB
2-Methylpropyl 2-N-methylaminobenzoateHMDB
Benzoic acid, 2-(methylamino)-, 2-methylpropyl esterHMDB
iso-Butyl N-methyl anthranilateHMDB
Isobutyl 2-(methylamino)benzoateHMDB
Isobutyl 2-N-methylaminobenzoateHMDB
2-Methylpropyl 2-(methylamino)benzoic acidGenerator
Chemical FormulaC12H17NO2
Average Molecular Weight207.2689
Monoisotopic Molecular Weight207.125928793
IUPAC Name2-methylpropyl 2-(methylamino)benzoate
Traditional Name2-methylpropyl 2-(methylamino)benzoate
CAS Registry Number65505-24-0
SMILES
CNC1=CC=CC=C1C(=O)OCC(C)C
InChI Identifier
InChI=1S/C12H17NO2/c1-9(2)8-15-12(14)10-6-4-5-7-11(10)13-3/h4-7,9,13H,8H2,1-3H3
InChI KeyWKYZGTHZBSYUFI-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
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
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 Solubility0.38 g/LALOGPS
logP2.64ALOGPS
logP3.34ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)19.58ChemAxon
pKa (Strongest Basic)2.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.02 m³·mol⁻¹ChemAxon
Polarizability23.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.43831661259
DarkChem[M-H]-146.91431661259
DeepCCS[M+H]+149.28330932474
DeepCCS[M-H]-146.92530932474
DeepCCS[M-2H]-181.56430932474
DeepCCS[M+Na]+156.17630932474
AllCCS[M+H]+146.832859911
AllCCS[M+H-H2O]+142.932859911
AllCCS[M+NH4]+150.432859911
AllCCS[M+Na]+151.532859911
AllCCS[M-H]-150.132859911
AllCCS[M+Na-2H]-150.832859911
AllCCS[M+HCOO]-151.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isobutyl N-methylanthranilateCNC1=CC=CC=C1C(=O)OCC(C)C2117.4Standard polar33892256
Isobutyl N-methylanthranilateCNC1=CC=CC=C1C(=O)OCC(C)C1643.9Standard non polar33892256
Isobutyl N-methylanthranilateCNC1=CC=CC=C1C(=O)OCC(C)C1625.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isobutyl N-methylanthranilate,1TMS,isomer #1CC(C)COC(=O)C1=CC=CC=C1N(C)[Si](C)(C)C1659.1Semi standard non polar33892256
Isobutyl N-methylanthranilate,1TMS,isomer #1CC(C)COC(=O)C1=CC=CC=C1N(C)[Si](C)(C)C1759.6Standard non polar33892256
Isobutyl N-methylanthranilate,1TBDMS,isomer #1CC(C)COC(=O)C1=CC=CC=C1N(C)[Si](C)(C)C(C)(C)C1856.5Semi standard non polar33892256
Isobutyl N-methylanthranilate,1TBDMS,isomer #1CC(C)COC(=O)C1=CC=CC=C1N(C)[Si](C)(C)C(C)(C)C1937.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isobutyl N-methylanthranilate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0536-9700000000-2bc008f97ecd97776f292017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isobutyl 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 - Isobutyl N-methylanthranilate 10V, Positive-QTOFsplash10-0a4i-9880000000-9d26c8a75fb5a15abdd82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl N-methylanthranilate 20V, Positive-QTOFsplash10-0a4i-9510000000-85a11285bf45bf8b563e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl N-methylanthranilate 40V, Positive-QTOFsplash10-0a4i-9300000000-130ea7ddc29df9c7a8d62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl N-methylanthranilate 10V, Negative-QTOFsplash10-0a4i-1590000000-fed18a870e27b574a4c22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl N-methylanthranilate 20V, Negative-QTOFsplash10-0a4i-2920000000-23cbca8d6be2b14ad68c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl N-methylanthranilate 40V, Negative-QTOFsplash10-0a4l-6900000000-f99dbf87e1c4e31d08322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl N-methylanthranilate 10V, Positive-QTOFsplash10-001i-0920000000-e3eaeff6d4e17bbc34fc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl N-methylanthranilate 20V, Positive-QTOFsplash10-001i-1900000000-48a9ae6b4237e00da0502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl N-methylanthranilate 40V, Positive-QTOFsplash10-0aou-9400000000-04613b3fa87f8d557ed42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl N-methylanthranilate 10V, Negative-QTOFsplash10-0a4i-0690000000-cc8220d9608051205b5c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl N-methylanthranilate 20V, Negative-QTOFsplash10-0a4i-0910000000-f2e756c1870bed121aa12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl N-methylanthranilate 40V, Negative-QTOFsplash10-0pb9-4910000000-f407f7d51ac0d42b989d2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB016825
KNApSAcK IDNot Available
Chemspider ID455495
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound522171
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 References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .