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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:42:19 UTC

Update Date

2021-09-26 23:04:22 UTC

HMDB ID

HMDB0252029

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Ethyl 3-aminobenzoate

Description

tricaine, also known as ai3-02743 or metacaine, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. tricaine is a moderately basic compound (based on its pKa). Used (in the form of its methanesulfonate salt) as an anaesthetic for fish. This compound has been identified in human blood as reported by (PMID: 31557052 ). Ethyl 3-aminobenzoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ethyl 3-aminobenzoate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   12                                                       
CONECT    3    4    5                                                       
CONECT    4    3    7                                                       
CONECT    5    3    8                                                       
CONECT    6    7    8                                                       
CONECT    7    4    6    9                                                  
CONECT    8    5    6   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
3-(Ethoxycarbonyl)aniline	ChEBI
3-Aminobenzoic acid ethyl ester	ChEBI
AI3-02743	ChEBI
Ethyl m-aminobenzoate	ChEBI
m-Aminobenzoic acid, ethyl ester	ChEBI
m-Ethoxycarbonylaniline	ChEBI
Metacaine	ChEBI
3-Aminobenzoic acid	Kegg
m-Aminobenzoate	Kegg
3-Aminobenzoate ethyl ester	Generator
Ethyl m-aminobenzoic acid	Generator
m-Aminobenzoate, ethyl ester	Generator
3-Aminobenzoate	Generator
m-Aminobenzoic acid	Generator
Tricaine hydrochloride	MeSH
Ethyl m-aminobenzoate methanesulfonate	MeSH
Tricaine methane sulfonate (CH3SO4)	MeSH
Ethyl 3-aminobenzoic acid	Generator
MS222 Compound	MeSH
Tricaine	MeSH

Chemical Formula

C₉H₁₁NO₂

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

IUPAC Name

ethyl 3-aminobenzoate

Traditional Name

tricaine

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1=CC(N)=CC=C1

InChI Identifier

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

InChI Key

ZMCBYSBVJIMENC-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
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 Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoate ester (CHEBI:81494 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.12	ALOGPS
logP	1.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	2.89	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	17.66 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
DeepCCS	[M+H]+	136.749	30932474
DeepCCS	[M-H]-	133.101	30932474
DeepCCS	[M-2H]-	170.438	30932474
DeepCCS	[M+Na]+	145.976	30932474
AllCCS	[M+H]+	135.8	32859911
AllCCS	[M+H-H2O]+	131.4	32859911
AllCCS	[M+NH4]+	139.9	32859911
AllCCS	[M+Na]+	141.1	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 3-aminobenzoate	CCOC(=O)C1=CC(N)=CC=C1	2606.7	Standard polar	33892256
Ethyl 3-aminobenzoate	CCOC(=O)C1=CC(N)=CC=C1	1508.1	Standard non polar	33892256
Ethyl 3-aminobenzoate	CCOC(=O)C1=CC(N)=CC=C1	1549.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 3-aminobenzoate,1TMS,isomer #1	CCOC(=O)C1=CC=CC(N[Si](C)(C)C)=C1	1691.6	Semi standard non polar	33892256
Ethyl 3-aminobenzoate,1TMS,isomer #1	CCOC(=O)C1=CC=CC(N[Si](C)(C)C)=C1	1707.5	Standard non polar	33892256
Ethyl 3-aminobenzoate,1TMS,isomer #1	CCOC(=O)C1=CC=CC(N[Si](C)(C)C)=C1	1995.1	Standard polar	33892256
Ethyl 3-aminobenzoate,2TMS,isomer #1	CCOC(=O)C1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C1	1707.7	Semi standard non polar	33892256
Ethyl 3-aminobenzoate,2TMS,isomer #1	CCOC(=O)C1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C1	1775.4	Standard non polar	33892256
Ethyl 3-aminobenzoate,2TMS,isomer #1	CCOC(=O)C1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C1	1925.5	Standard polar	33892256
Ethyl 3-aminobenzoate,1TBDMS,isomer #1	CCOC(=O)C1=CC=CC(N[Si](C)(C)C(C)(C)C)=C1	1932.7	Semi standard non polar	33892256
Ethyl 3-aminobenzoate,1TBDMS,isomer #1	CCOC(=O)C1=CC=CC(N[Si](C)(C)C(C)(C)C)=C1	1905.0	Standard non polar	33892256
Ethyl 3-aminobenzoate,1TBDMS,isomer #1	CCOC(=O)C1=CC=CC(N[Si](C)(C)C(C)(C)C)=C1	2137.8	Standard polar	33892256
Ethyl 3-aminobenzoate,2TBDMS,isomer #1	CCOC(=O)C1=CC=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2126.1	Semi standard non polar	33892256
Ethyl 3-aminobenzoate,2TBDMS,isomer #1	CCOC(=O)C1=CC=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2156.2	Standard non polar	33892256
Ethyl 3-aminobenzoate,2TBDMS,isomer #1	CCOC(=O)C1=CC=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2149.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 3-aminobenzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3900000000-321ae4d11edd6870b6b1	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 3-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 3-aminobenzoate 30V, Positive-QTOF	splash10-00ou-9100000000-f96538fbbfac7373f466	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 40V, Positive-QTOF	splash10-016r-9000000000-80eb35ce65ff7bad4ddb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 10V, Positive-QTOF	splash10-014r-1900000000-ea658d46ba08eb9565b9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 0V, Positive-QTOF	splash10-014i-0900000000-6a59332ccc40e636cb3c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 30V, Positive-QTOF	splash10-01dl-9200000000-fb27416ed3de3d8513a9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 0V, Positive-QTOF	splash10-014i-0900000000-bafc166d188410c2bc20	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 20V, Positive-QTOF	splash10-000i-7900000000-c90179aa8ae9ad332a72	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 10V, Positive-QTOF	splash10-00kr-0900000000-9873184b3241452f1d7c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 10V, Positive-QTOF	splash10-00kr-0900000000-5272c36eaf9d8191f4f3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 30V, Positive-QTOF	splash10-016u-9100000000-4525e5f7d7addedd9808	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 10V, Positive-QTOF	splash10-01bc-3900000000-b021f23981abfcefd4d7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 20V, Positive-QTOF	splash10-00du-4900000000-c3063bc96696df3a6691	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 40V, Positive-QTOF	splash10-006x-9400000000-01199df95c80940cf1e1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 10V, Negative-QTOF	splash10-03di-0900000000-c426d7c17f89faa52595	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 20V, Negative-QTOF	splash10-03dl-4900000000-d46fd6652bc64ba26d43	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-aminobenzoate 40V, Negative-QTOF	splash10-0006-9000000000-ebd80b5f30a3dfa24252	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C18090

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tricaine_mesylate

METLIN ID

Not Available

PubChem Compound

11400

PDB ID

Not Available

ChEBI ID

81494

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Ethyl 3-aminobenzoate (HMDB0252029)

MOL for HMDB0252029 (Ethyl 3-aminobenzoate)

3D MOL for HMDB0252029 (Ethyl 3-aminobenzoate)

3D SDF for HMDB0252029 (Ethyl 3-aminobenzoate)

3D-SDF for HMDB0252029 (Ethyl 3-aminobenzoate)

PDB for HMDB0252029 (Ethyl 3-aminobenzoate)

3D PDB for HMDB0252029 (Ethyl 3-aminobenzoate)

SMILES for HMDB0252029 (Ethyl 3-aminobenzoate)

INCHI for HMDB0252029 (Ethyl 3-aminobenzoate)

Structure for HMDB0252029 (Ethyl 3-aminobenzoate)

3D Structure for HMDB0252029 (Ethyl 3-aminobenzoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra