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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:57:47 UTC

Update Date

2023-02-21 17:23:58 UTC

HMDB ID

HMDB0034169

Secondary Accession Numbers

HMDB34169

Metabolite Identification

Common Name

Methyl N-methylanthranilate

Description

Methyl 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   12                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    8    9                                                  
CONECT    8    6    7   10                                                  
CONECT    9    7   11   12                                                  
CONECT   10    1    8                                                       
CONECT   11    9                                                            
CONECT   12    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Methylaminobenzoic acid methyl ester	ChEBI
2-Methylaminomethyl benzoate	ChEBI
Dimethyl anthranilate	ChEBI
Methyl methanthranilate	ChEBI
Methyl methylaminobenzoate	ChEBI
Methyl methylanthranilate	ChEBI
Methyl N-methyl anthranylate	ChEBI
N-Methylanthranilic acid, methyl ester	ChEBI
2-Methylaminobenzoate methyl ester	Generator
2-Methylaminomethyl benzoic acid	Generator
Dimethyl anthranilic acid	Generator
Methyl methanthranilic acid	Generator
Methyl methylaminobenzoic acid	Generator
Methyl methylanthranilic acid	Generator
Methyl N-methyl anthranylic acid	Generator
N-Methylanthranilate, methyl ester	Generator
Methyl N-methylanthranilic acid	Generator
2-methylamino-Benzoic acid methyl ester	HMDB
Anthranilic acid, N-methyl-, methyl ester	HMDB
Benzoic acid, 2-(methylamino)-, methyl ester	HMDB
FEMA 2718	HMDB
Methyl 2-(methylamino)benzoate	HMDB
Methyl 2-methylaminobenzoate	HMDB
Methyl benzoate, 2-methylamino	HMDB
Methyl N-methyl anthranilate	HMDB
Methyl N-methyl-O-anthranilate	HMDB
Methyl O-(methylamino)benzoate	HMDB
Methyl-2-(N-methylamino)benzoate	HMDB
Methyl-N-methylanthranilate	HMDB
N-Methyl methyl anthranilate	HMDB
Methyl 2-(methylamino)benzoic acid	Generator
Methyl N-methylanthranilate	MeSH

Chemical Formula

C₉H₁₁NO₂

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

IUPAC Name

methyl 2-(methylamino)benzoate

Traditional Name

methyl 2-(methylamino)benzoate

CAS Registry Number

85-91-6

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 Key

GVOWHGSUZUUUDR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034169)
Cytoplasm (HMDB: HMDB0034169)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034169)

Source

Exogenous

Exogenous (HMDB: HMDB0034169)

Food

Food (HMDB: HMDB0034169)

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0034169)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0034169)

Biological role

Nutrient (HMDB: HMDB0034169)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	19 °C	Not Available
Boiling Point	255.00 to 256.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	475 mg/L @ 20 °C (exp)	The Good Scents Company Information System
LogP	2.531 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.69 g/L	ALOGPS
logP	1.75	ALOGPS
logP	2.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	19.59	ChemAxon
pKa (Strongest Basic)	2.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.28 m³·mol⁻¹	ChemAxon
Polarizability	17.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.943	31661259
DarkChem	[M-H]-	134.421	31661259
DeepCCS	[M+H]+	129.063	30932474
DeepCCS	[M-H]-	125.229	30932474
DeepCCS	[M-2H]-	162.675	30932474
DeepCCS	[M+Na]+	138.216	30932474
AllCCS	[M+H]+	135.6	32859911
AllCCS	[M+H-H2O]+	131.2	32859911
AllCCS	[M+NH4]+	139.7	32859911
AllCCS	[M+Na]+	140.9	32859911
AllCCS	[M-H]-	134.4	32859911
AllCCS	[M+Na-2H]-	135.5	32859911
AllCCS	[M+HCOO]-	136.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl N-methylanthranilate	CNC1=CC=CC=C1C(=O)OC	2071.2	Standard polar	33892256
Methyl N-methylanthranilate	CNC1=CC=CC=C1C(=O)OC	1446.1	Standard non polar	33892256
Methyl N-methylanthranilate	CNC1=CC=CC=C1C(=O)OC	1407.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl N-methylanthranilate,1TMS,isomer #1	COC(=O)C1=CC=CC=C1N(C)[Si](C)(C)C	1474.2	Semi standard non polar	33892256
Methyl N-methylanthranilate,1TMS,isomer #1	COC(=O)C1=CC=CC=C1N(C)[Si](C)(C)C	1585.9	Standard non polar	33892256
Methyl N-methylanthranilate,1TBDMS,isomer #1	COC(=O)C1=CC=CC=C1N(C)[Si](C)(C)C(C)(C)C	1674.5	Semi standard non polar	33892256
Methyl N-methylanthranilate,1TBDMS,isomer #1	COC(=O)C1=CC=CC=C1N(C)[Si](C)(C)C(C)(C)C	1778.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl N-methylanthranilate GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-3900000000-71dd24a94747bc71cff4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl N-methylanthranilate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 10V, Positive-QTOF	splash10-014i-0900000000-af87edaa1391f623356d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 20V, Positive-QTOF	splash10-0159-0900000000-b7d3f91cccbccb6109a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 40V, Positive-QTOF	splash10-0pc0-8900000000-7900a388e2a9753b49c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 10V, Negative-QTOF	splash10-03di-0900000000-f0fe7fc3060819b5a0a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 20V, Negative-QTOF	splash10-03di-0900000000-5e8fda07dbb8dc499d1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 40V, Negative-QTOF	splash10-0ue9-4900000000-15fa8f5d7c70fff9299d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 10V, Positive-QTOF	splash10-001i-0900000000-409c0f325aa5ec0f6a9f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 20V, Positive-QTOF	splash10-001i-0900000000-4b51ded7059986756833	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 40V, Positive-QTOF	splash10-0ldi-9200000000-1b920371adb5ce1a24fc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 10V, Negative-QTOF	splash10-03di-0900000000-a7afb973c05f34cd28a7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 20V, Negative-QTOF	splash10-0a4i-0900000000-4c001580e59aedfbd58c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl N-methylanthranilate 40V, Negative-QTOF	splash10-0ik9-7900000000-0fe6bf21e9c43f76d242	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012455

KNApSAcK ID

Not Available

Chemspider ID

21108245

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6826

PDB ID

Not Available

ChEBI ID

142267

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1004392

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methyl N-methylanthranilate (HMDB0034169)

MOL for HMDB0034169 (Methyl N-methylanthranilate)

3D MOL for HMDB0034169 (Methyl N-methylanthranilate)

3D SDF for HMDB0034169 (Methyl N-methylanthranilate)

3D-SDF for HMDB0034169 (Methyl N-methylanthranilate)

PDB for HMDB0034169 (Methyl N-methylanthranilate)

3D PDB for HMDB0034169 (Methyl N-methylanthranilate)

SMILES for HMDB0034169 (Methyl N-methylanthranilate)

INCHI for HMDB0034169 (Methyl N-methylanthranilate)

Structure for HMDB0034169 (Methyl N-methylanthranilate)

3D Structure for HMDB0034169 (Methyl N-methylanthranilate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra