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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:20:03 UTC

Update Date

2023-02-21 17:23:27 UTC

HMDB ID

HMDB0033589

Secondary Accession Numbers

HMDB33589

Metabolite Identification

Common Name

Ethyl 2-aminobenzoate

Description

Ethyl 2-aminobenzoate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Ethyl 2-aminobenzoate is a sweet, blossom, and floral tasting compound. Ethyl 2-aminobenzoate has been detected, but not quantified in, citrus and fruits. This could make ethyl 2-aminobenzoate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Ethyl 2-aminobenzoate.

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   6.160   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    2                                                            
CONECT    2    1   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    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
Ethyl 2-aminobenzoic acid	Generator
2-(Ethoxycarbonyl)aniline	HMDB
2-Aminobenzoic acid ethyl ester	HMDB
2-Aminobenzoic acid, ethyl ester	HMDB
2-Carboethoxyaniline	HMDB
Anthranilic acid, ethyl ester	HMDB
Anthranilic acid, ethyl ester (6ci,7ci,8ci)	HMDB
Benzoic acid, 2-amino-, ethyl ester	HMDB
Benzoic acid, O-amino-, ethyl ester	HMDB
Ethyl anthranilate	HMDB
Ethyl O-aminobenzoate	HMDB
FEMA 2421	HMDB
O-(Ethoxycarbonyl)aniline	HMDB
Ethyl anthranilic acid	Generator

Chemical Formula

C₉H₁₁NO₂

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

IUPAC Name

ethyl 2-aminobenzoate

Traditional Name

ethyl 2-aminobenzoate

CAS Registry Number

87-25-2

SMILES

CCOC(=O)C1=CC=CC=C1N

InChI Identifier

InChI=1S/C9H11NO2/c1-2-12-9(11)7-5-3-4-6-8(7)10/h3-6H,2,10H2,1H3

InChI Key

TWLLPUMZVVGILS-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
Vinylogous amide
Amino acid or derivatives
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033589)
Cell membrane (HMDB: HMDB0033589)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033589)

Source

Exogenous

Exogenous (HMDB: HMDB0033589)

Food

Food (HMDB: HMDB0033589)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033589)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033589)

Biological role

Nutrient (HMDB: HMDB0033589)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	13 °C	Not Available
Boiling Point	129.00 to 130.00 °C. @ 9.00 mm Hg	The Good Scents Company Information System
Water Solubility	413.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.57	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.82 g/L	ALOGPS
logP	1.95	ALOGPS
logP	2.15	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	19.4	ChemAxon
pKa (Strongest Basic)	2.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.53 m³·mol⁻¹	ChemAxon
Polarizability	17.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.165	31661259
DarkChem	[M-H]-	133.787	31661259
DeepCCS	[M+H]+	135.651	30932474
DeepCCS	[M-H]-	132.992	30932474
DeepCCS	[M-2H]-	169.409	30932474
DeepCCS	[M+Na]+	144.702	30932474
AllCCS	[M+H]+	136.0	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.2	32859911
AllCCS	[M-H]-	135.7	32859911
AllCCS	[M+Na-2H]-	136.8	32859911
AllCCS	[M+HCOO]-	138.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 2-aminobenzoate	CCOC(=O)C1=CC=CC=C1N	2400.5	Standard polar	33892256
Ethyl 2-aminobenzoate	CCOC(=O)C1=CC=CC=C1N	1426.6	Standard non polar	33892256
Ethyl 2-aminobenzoate	CCOC(=O)C1=CC=CC=C1N	1433.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 2-aminobenzoate,1TMS,isomer #1	CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C	1568.4	Semi standard non polar	33892256
Ethyl 2-aminobenzoate,1TMS,isomer #1	CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C	1604.8	Standard non polar	33892256
Ethyl 2-aminobenzoate,2TMS,isomer #1	CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1604.8	Semi standard non polar	33892256
Ethyl 2-aminobenzoate,2TMS,isomer #1	CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1678.4	Standard non polar	33892256
Ethyl 2-aminobenzoate,1TBDMS,isomer #1	CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C	1782.8	Semi standard non polar	33892256
Ethyl 2-aminobenzoate,1TBDMS,isomer #1	CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C	1816.5	Standard non polar	33892256
Ethyl 2-aminobenzoate,2TBDMS,isomer #1	CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2026.9	Semi standard non polar	33892256
Ethyl 2-aminobenzoate,2TBDMS,isomer #1	CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2063.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ethyl 2-aminobenzoate EI-B (Non-derivatized)	splash10-014i-5900000000-93092db3cfda9502465f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl 2-aminobenzoate EI-B (Non-derivatized)	splash10-014i-5900000000-93092db3cfda9502465f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2-aminobenzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2900000000-c63fe5fcae725bb84646	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2-aminobenzoate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 2-aminobenzoate LC-ESI-qTof , Positive-QTOF	splash10-000i-0290000000-343c52391942cb7c0f2b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 2-aminobenzoate , positive-QTOF	splash10-00di-1911000000-d9aa52a8aababe9fb850	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 15V, Positive-QTOF	splash10-0a4i-0900000000-0b283a753d9fd70a239d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 45V, Positive-QTOF	splash10-0a4i-0900000000-45b533b3e864fd54b21c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 60V, Positive-QTOF	splash10-0a4i-2900000000-5d0dde110b59b901005b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 75V, Positive-QTOF	splash10-0a4l-8900000000-920aa76e7081f14aeca6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 90V, Positive-QTOF	splash10-052f-9300000000-8dcad614be86fbe6b027	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 10V, Positive-QTOF	splash10-014j-0900000000-dc54fffc23390e4d8bd5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 20V, Positive-QTOF	splash10-00xr-2900000000-fb8eef570a236ab3fc5f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 40V, Positive-QTOF	splash10-0g2c-9300000000-905e3245525fe407e8e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 10V, Negative-QTOF	splash10-03di-2900000000-8670ab8bf9198bb0fc83	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 20V, Negative-QTOF	splash10-0296-6900000000-16da7537d83e037559b3	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 40V, Negative-QTOF	splash10-0006-9200000000-bee4985e963f8c32e0bc	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 10V, Positive-QTOF	splash10-00di-0900000000-aad7be030fa57b13df23	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 20V, Positive-QTOF	splash10-00di-2900000000-bdbc87d0a98784a28cc8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 40V, Positive-QTOF	splash10-006x-9300000000-d11cdef78720a18437b5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 10V, Negative-QTOF	splash10-03dl-4900000000-ef12f2bf710ec607f54b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 20V, Negative-QTOF	splash10-0006-9200000000-9e16c5ad80c4b4028f30	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-aminobenzoate 40V, Negative-QTOF	splash10-0006-9000000000-eef4c1f804c025cbb978	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

Membrane

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

FDB011666

KNApSAcK ID

Not Available

Chemspider ID

21106112

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6877

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1014531

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 Ethyl 2-aminobenzoate (HMDB0033589)

MOL for HMDB0033589 (Ethyl 2-aminobenzoate)

3D MOL for HMDB0033589 (Ethyl 2-aminobenzoate)

3D SDF for HMDB0033589 (Ethyl 2-aminobenzoate)

3D-SDF for HMDB0033589 (Ethyl 2-aminobenzoate)

PDB for HMDB0033589 (Ethyl 2-aminobenzoate)

3D PDB for HMDB0033589 (Ethyl 2-aminobenzoate)

SMILES for HMDB0033589 (Ethyl 2-aminobenzoate)

INCHI for HMDB0033589 (Ethyl 2-aminobenzoate)

Structure for HMDB0033589 (Ethyl 2-aminobenzoate)

3D Structure for HMDB0033589 (Ethyl 2-aminobenzoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra