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Showing NP-Card for Methyl anthranilate (NP0045159)

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Record Information
Version2.0
Created at2022-03-10 18:58:58 UTC
Updated at2022-03-10 22:21:43 UTC
NP-MRD IDNP0045159
Secondary Accession NumbersNone
Natural Product 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
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045159 (Methyl anthranilate)


  Mrv1652303202019012D          

 11 11  0  0  0  0            999 V2000
    0.3573   -1.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3560    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706    1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3560    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    1.2369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0045159 (Methyl anthranilate)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
    3.3646    0.7100   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9555    0.6842   -0.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1830   -0.4241   -0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7512   -1.4288   -0.8794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2421   -0.4967   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9234   -1.6537   -0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3000   -1.7127   -0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9642   -0.6312    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2451    0.5072    0.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797    0.5957    0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    1.7546    0.6863 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7772   -0.3204   -0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8509    1.2730    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5644    1.2343   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603   -2.5338   -0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8184   -2.6303   -0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0220   -0.7088    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7721    1.3587    1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3088    2.6136    0.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6102    1.8093    1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
 11 20  1  0
M  END
Download

3D SDF for NP0045159 (Methyl anthranilate)


  Mrv1652303202019012D          

 11 11  0  0  0  0            999 V2000
    0.3573   -1.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3560    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706    1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3560    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    1.2369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045159

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
VAMXMNNIEUEQDV-UHFFFAOYSA-N

> <FORMULA>
C8H9NO2

> <MOLECULAR_WEIGHT>
151.1626

> <EXACT_MASS>
151.063328537

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.221714344803988

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-aminobenzoate

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
1.7977968260000001

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.404528195387766

> <JCHEM_PKA_STRONGEST_BASIC>
2.122186885345067

> <JCHEM_POLAR_SURFACE_AREA>
52.32000000000001

> <JCHEM_REFRACTIVITY>
42.7837

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl anthranilate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0045159 (Methyl anthranilate)

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PDB for NP0045159 (Methyl anthranilate)
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0       0.667  -2.309   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.665   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.998  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.332   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.332   1.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.998   2.309   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.665   1.539   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.667   2.309   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       2.001   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.332  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8                                                            
CONECT   10    2   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0045159 (Methyl anthranilate)
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SMILES for NP0045159 (Methyl anthranilate)
COC(=O)C1=CC=CC=C1N
Download
INCHI for NP0045159 (Methyl anthranilate)
InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
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View in JSmol
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 Mass151.1626 Da
Monoisotopic Mass151.06333 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acokanthera oblongifoliaLOTUS Database
Averrhoa carambolaLOTUS Database
Cannabis sativaNULL
      Not Available
Citrus aurantiifoliaFooDB
Citrus aurantiumPlant
Citrus hystrixPlant
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiPlant
Citrus reticulataFooDB
Citrus sinensisLOTUS Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Hesperis matronalisPlant
Jasminum grandiflorumPlant
Jasminum sambacLOTUS Database
Lonicera fulvotomentosaLOTUS Database
Mentha arvensisLOTUS Database
Murraya paniculataPlant
Narcissus tazettaLOTUS Database
Theobroma cacaoFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
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  
Good Scents IDNot Available
References
General References
  1. Pankiw T: Reducing honey bee defensive responses and social wasp colonization with methyl anthranilate. J Med Entomol. 2009 Jul;46(4):782-8. doi: 10.1603/033.046.0408. [PubMed:19645280  ] 
  2. Kollner TG, Lenk C, Zhao N, Seidl-Adams I, Gershenzon J, Chen F, Degenhardt J: Herbivore-induced SABATH methyltransferases of maize that methylate anthranilic acid using s-adenosyl-L-methionine. Plant Physiol. 2010 Aug;153(4):1795-807. doi: 10.1104/pp.110.158360. Epub 2010 Jun 2. [PubMed:20519632  ] 
  3. Robacker DC, Massa MJ, Sacchetti P, Bartelt RJ: A novel attractant for Anastrepha ludens (Diptera: Tephritidae) from a Concord grape product. J Econ Entomol. 2011 Aug;104(4):1195-203. doi: 10.1603/ec10220. [PubMed:21882683  ] 
  4. Mann RS, Ali JG, Hermann SL, Tiwari S, Pelz-Stelinski KS, Alborn HT, Stelinski LL: Induced release of a plant-defense volatile 'deceptively' attracts insect vectors to plants infected with a bacterial pathogen. PLoS Pathog. 2012;8(3):e1002610. doi: 10.1371/journal.ppat.1002610. Epub 2012 Mar 22. [PubMed:22457628  ] 
  5. Esther A, Tilcher R, Jacob J: Assessing the effects of three potential chemical repellents to prevent bird damage to corn seeds and seedlings. Pest Manag Sci. 2013 Mar;69(3):425-30. doi: 10.1002/ps.3288. Epub 2012 Apr 12. [PubMed:22499556  ]