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Showing metabocard for Methyl 2-aminobenzoate (HMDB0029703)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:09 UTC
Update Date2023-02-21 17:19:04 UTC
HMDB IDHMDB0029703
Secondary Accession Numbers
  • HMDB29703
Metabolite Identification
Common NameMethyl 2-aminobenzoate
DescriptionMethyl 2-aminobenzoate, also known as 2-carbomethoxyaniline or 2-(methoxycarbonyl)aniline, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. 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 limes (Citrus aurantiifolia), herbal tea, alcoholic beverages, teas (Camellia sinensis), and cocoa beans (Theobroma cacao). This could make methyl 2-aminobenzoate a potential biomarker for the consumption of these foods. Methyl 2-aminobenzoate 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 significant number of articles have been published on Methyl 2-aminobenzoate.
Structure
Data?1676999944
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029703 (Methyl 2-aminobenzoate)

  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
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3D MOL for HMDB0029703 (Methyl 2-aminobenzoate)

HMDB0029703
     RDKit          3D
Methyl 2-aminobenzoate
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.4593    0.1745    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0629    0.3772    0.2970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084   -0.6518   -0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6766   -1.7843   -0.3288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536   -0.4979    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1016   -1.5343   -0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -1.4132   -0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178   -0.1955    0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2053    0.8926    0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227    0.7104    0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0330    1.8294    0.6709 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    0.5555    1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8423    0.8054   -0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -0.8644   -0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6672   -2.4877   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564   -2.2153   -0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0862   -0.0361    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6669    1.8288    0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6707    2.2345    0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563    2.2722    1.6087 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
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3D SDF for HMDB0029703 (Methyl 2-aminobenzoate)

  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>
HMDB0029703

> <DATABASE_NAME>
hmdb

> <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 HMDB0029703 (Methyl 2-aminobenzoate)

HMDB0029703
     RDKit          3D
Methyl 2-aminobenzoate
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.4593    0.1745    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0629    0.3772    0.2970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084   -0.6518   -0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6766   -1.7843   -0.3288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536   -0.4979    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1016   -1.5343   -0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -1.4132   -0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178   -0.1955    0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2053    0.8926    0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227    0.7104    0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0330    1.8294    0.6709 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    0.5555    1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8423    0.8054   -0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -0.8644   -0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6672   -2.4877   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564   -2.2153   -0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0862   -0.0361    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6669    1.8288    0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6707    2.2345    0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563    2.2722    1.6087 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
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PDB for HMDB0029703 (Methyl 2-aminobenzoate)

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 HMDB0029703 (Methyl 2-aminobenzoate)

COMPND    HMDB0029703
HETATM    1  C1  UNL     1       3.459   0.175   0.267  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.063   0.377   0.297  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.208  -0.652  -0.014  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.677  -1.784  -0.329  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.254  -0.498   0.001  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.102  -1.534  -0.312  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.473  -1.413  -0.305  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.018  -0.195   0.033  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.205   0.893   0.360  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.823   0.710   0.335  1.00  0.00           C  
HETATM   11  N1  UNL     1      -0.033   1.829   0.671  1.00  0.00           N  
HETATM   12  H1  UNL     1       3.978   0.555   1.163  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.842   0.805  -0.588  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.742  -0.864  -0.003  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.667  -2.488  -0.576  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.156  -2.215  -0.548  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.086  -0.036   0.057  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.667   1.829   0.619  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.671   2.234   0.021  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.156   2.272   1.609  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   10
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9   17
CONECT    9   10   10   18
CONECT   10   11
CONECT   11   19   20
END
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SMILES for HMDB0029703 (Methyl 2-aminobenzoate)

COC(=O)C1=CC=CC=C1N
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INCHI for HMDB0029703 (Methyl 2-aminobenzoate)

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 JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H9NO2
Average Molecular Weight151.1626
Monoisotopic Molecular Weight151.063328537
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
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point24 - 25 °CNot Available
Boiling Point238.00 to 241.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2.85 mg/mL at 25 °CNot Available
LogP1.88Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008211
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.. .