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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-03-07 16:38:32 UTC

Update Date

2023-02-21 17:15:56 UTC

HMDB ID

HMDB0001891

Secondary Accession Numbers

HMDB0002129
HMDB01891
HMDB02129

Metabolite Identification

Common Name

m-Aminobenzoic acid

Description

m-Aminobenzoic acid (also known as 3-aminobenzoic acid or MABA) is an organic compound with the molecular formula H2NC6H4CO2H. MABA is a white solid, although commercial samples are often colored. It is only slightly soluble in water. It is soluble in acetone, boiling water, hot alcohol, hot chloroform and ether. It consists of a benzene ring substituted with an amino group and a carboxylic acid. m-Aminobenzoic acid belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. Outside of the human body, m-Aminobenzoic acid has been detected, but not quantified in cow milk. This could make m-aminobenzoic acid a potential biomarker for the consumption of these foods.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Aminobenzoesaeure	ChEBI
3-Carboxyaniline	ChEBI
m-Aminobenzoesaeure	ChEBI
m-Carboxyaniline	ChEBI
MABA	ChEBI
m-Aminobenzoate	Generator
Meta-aminobenzoic acid	MeSH
3-Aminobenzoic acid, monosodium salt	MeSH
Aniline-3-carboxylate	HMDB
3-Aminobenzoate	HMDB, Generator
3-Aminobenzoic acid	HMDB
Aniline-3-carboxylic acid	HMDB
m-Amonibenzoate	HMDB
m-Amonibenzoic acid	HMDB
m-Aminobenzoic acid	ChEBI

Chemical Formula

C₇H₇NO₂

Average Molecular Weight

137.136

Monoisotopic Molecular Weight

137.047678473

IUPAC Name

3-aminobenzoic acid

Traditional Name

gabaculine

CAS Registry Number

99-05-8

SMILES

NC1=CC=CC(=C1)C(O)=O

InChI Identifier

InChI=1S/C7H7NO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,8H2,(H,9,10)

InChI Key

XFDUHJPVQKIXHO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzoic acids

Alternative Parents

Substituents

Aminobenzoic acid
Benzoic acid
Benzoyl
Aniline or substituted anilines
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
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

aminobenzoic acid (CHEBI:42682 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001891)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001891)

Source

Exogenous

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Environmental role

Environmental contaminant (HMDB: HMDB0001891)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001891)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	173 °C	Not Available
Boiling Point	352.55 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	5.9 mg/mL at 15 °C	Not Available
LogP	0.65	SANGSTER (1994)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.36 g/L	ALOGPS
logP	0.93	ALOGPS
logP	0.63	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.81	ChemAxon
pKa (Strongest Basic)	3.27	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.01 m³·mol⁻¹	ChemAxon
Polarizability	13.41 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	128.49	31661259
DarkChem	[M-H]-	126.977	31661259
AllCCS	[M+H]+	129.228	32859911
AllCCS	[M-H]-	124.275	32859911
DeepCCS	[M+H]+	124.599	30932474
DeepCCS	[M-H]-	120.927	30932474
DeepCCS	[M-2H]-	158.24	30932474
DeepCCS	[M+Na]+	133.39	30932474
AllCCS	[M+H]+	129.2	32859911
AllCCS	[M+H-H2O]+	124.6	32859911
AllCCS	[M+NH4]+	133.6	32859911
AllCCS	[M+Na]+	134.8	32859911
AllCCS	[M-H]-	124.3	32859911
AllCCS	[M+Na-2H]-	125.9	32859911
AllCCS	[M+HCOO]-	127.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
m-Aminobenzoic acid	NC1=CC=CC(=C1)C(O)=O	3273.6	Standard polar	33892256
m-Aminobenzoic acid	NC1=CC=CC(=C1)C(O)=O	1552.8	Standard non polar	33892256
m-Aminobenzoic acid	NC1=CC=CC(=C1)C(O)=O	1536.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
m-Aminobenzoic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC(N)=C1	1595.7	Semi standard non polar	33892256
m-Aminobenzoic acid,1TMS,isomer #2	C[Si](C)(C)NC1=CC=CC(C(=O)O)=C1	1725.4	Semi standard non polar	33892256
m-Aminobenzoic acid,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C)=C1	1725.9	Semi standard non polar	33892256
m-Aminobenzoic acid,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C)=C1	1750.8	Standard non polar	33892256
m-Aminobenzoic acid,2TMS,isomer #1	C[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C)=C1	1829.2	Standard polar	33892256
m-Aminobenzoic acid,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C	1770.1	Semi standard non polar	33892256
m-Aminobenzoic acid,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C	1868.2	Standard non polar	33892256
m-Aminobenzoic acid,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C	1954.8	Standard polar	33892256
m-Aminobenzoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C1	1725.6	Semi standard non polar	33892256
m-Aminobenzoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C1	1804.6	Standard non polar	33892256
m-Aminobenzoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C1	1763.3	Standard polar	33892256
m-Aminobenzoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(N)=C1	1834.2	Semi standard non polar	33892256
m-Aminobenzoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC(C(=O)O)=C1	2013.1	Semi standard non polar	33892256
m-Aminobenzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1	2178.3	Semi standard non polar	33892256
m-Aminobenzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1	2154.6	Standard non polar	33892256
m-Aminobenzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1	2109.1	Standard polar	33892256
m-Aminobenzoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C(C)(C)C	2240.3	Semi standard non polar	33892256
m-Aminobenzoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C(C)(C)C	2240.1	Standard non polar	33892256
m-Aminobenzoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C(C)(C)C	2125.2	Standard polar	33892256
m-Aminobenzoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2380.8	Semi standard non polar	33892256
m-Aminobenzoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2412.9	Standard non polar	33892256
m-Aminobenzoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2153.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - m-Aminobenzoic acid EI-B (Non-derivatized)	splash10-000i-4900000000-e768f284b0ad9fa688a5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - m-Aminobenzoic acid EI-B (Non-derivatized)	splash10-000i-4900000000-e768f284b0ad9fa688a5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Aminobenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-01bi-6900000000-5055dc85abc93a87c646	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Aminobenzoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-3900000000-d96d075152745c6f5d23	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Aminobenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Aminobenzoic acid 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 - m-Aminobenzoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-3900000000-b6cb655f6ded12c673de	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - m-Aminobenzoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-016r-9100000000-47171cdc0050a0ba58f3	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - m-Aminobenzoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-016r-9000000000-3d75db04ccdf6d696d3f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - m-Aminobenzoic acid LC-ESI-ITFT , positive-QTOF	splash10-000i-1900000000-b99ac73c3ae9561d99c9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - m-Aminobenzoic acid 50V, Positive-QTOF	splash10-000i-1900000000-3539179dacc0af3e1b25	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - m-Aminobenzoic acid 10V, Negative-QTOF	splash10-0006-9400000000-22a00bff4eaf264419f9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 10V, Positive-QTOF	splash10-000i-0900000000-caa9e00153a3a1612268	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 20V, Positive-QTOF	splash10-000i-2900000000-96b9acdf67eab6c3bf9c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 40V, Positive-QTOF	splash10-014i-9100000000-f6bbcf082a3b9e2d43f7	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 10V, Negative-QTOF	splash10-000i-3900000000-2efea194138ca00e98d5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 20V, Negative-QTOF	splash10-000f-9500000000-d840735b2d7650a4af0c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 40V, Negative-QTOF	splash10-0006-9000000000-db71e4a65c0a6b2b2c08	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 10V, Negative-QTOF	splash10-000f-9800000000-0898c9a8e0c1ece2e439	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 20V, Negative-QTOF	splash10-0006-9000000000-eef4c1f804c025cbb978	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 40V, Negative-QTOF	splash10-0006-9000000000-172bdc125075867d5bcb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 10V, Positive-QTOF	splash10-000i-3900000000-2aad2dc63caed09f95d9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 20V, Positive-QTOF	splash10-006x-8900000000-724130510a7832c96f38	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Aminobenzoic acid 40V, Positive-QTOF	splash10-0fr6-9000000000-8812b1e7f3cb93067efa	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.07 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02054

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022725

KNApSAcK ID

Not Available

Chemspider ID

7141

KEGG Compound ID

Not Available

BioCyc ID

HMDB01891

BiGG ID

Not Available

Wikipedia Link

3-Aminobenzoic_acid

METLIN ID

6374

PubChem Compound

7419

PDB ID

Not Available

ChEBI ID

42682

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1187341

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Wachsman JT: The beneficial effects of dietary restriction: reduced oxidative damage and enhanced apoptosis. Mutat Res. 1996 Feb 19;350(1):25-34. [PubMed:8657188 ]

Showing metabocard for m-Aminobenzoic acid (HMDB0001891)

MOL for HMDB0001891 (m-Aminobenzoic acid)

3D MOL for HMDB0001891 (m-Aminobenzoic acid)

3D SDF for HMDB0001891 (m-Aminobenzoic acid)

3D-SDF for HMDB0001891 (m-Aminobenzoic acid)

PDB for HMDB0001891 (m-Aminobenzoic acid)

3D PDB for HMDB0001891 (m-Aminobenzoic acid)

SMILES for HMDB0001891 (m-Aminobenzoic acid)

INCHI for HMDB0001891 (m-Aminobenzoic acid)

Structure for HMDB0001891 (m-Aminobenzoic acid)

3D Structure for HMDB0001891 (m-Aminobenzoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra