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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-03-07 16:38:32 UTC
Update Date2023-02-21 17:15:56 UTC
HMDB IDHMDB0001891
Secondary Accession Numbers
  • HMDB0002129
  • HMDB01891
  • HMDB02129
Metabolite Identification
Common Namem-Aminobenzoic acid
Descriptionm-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
Data?1676999756
Synonyms
ValueSource
3-AminobenzoesaeureChEBI
3-CarboxyanilineChEBI
m-AminobenzoesaeureChEBI
m-CarboxyanilineChEBI
MABAChEBI
m-AminobenzoateGenerator
Meta-aminobenzoic acidMeSH
3-Aminobenzoic acid, monosodium saltMeSH
Aniline-3-carboxylateHMDB
3-AminobenzoateHMDB, Generator
3-Aminobenzoic acidHMDB
Aniline-3-carboxylic acidHMDB
m-AmonibenzoateHMDB
m-Amonibenzoic acidHMDB
m-Aminobenzoic acidChEBI
Chemical FormulaC7H7NO2
Average Molecular Weight137.136
Monoisotopic Molecular Weight137.047678473
IUPAC Name3-aminobenzoic acid
Traditional Namegabaculine
CAS Registry Number99-05-8
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 KeyXFDUHJPVQKIXHO-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point173 °CNot Available
Boiling Point352.55 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility5.9 mg/mL at 15 °CNot Available
LogP0.65SANGSTER (1994)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.36 g/LALOGPS
logP0.93ALOGPS
logP0.63ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.81ChemAxon
pKa (Strongest Basic)3.27ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m³·mol⁻¹ChemAxon
Polarizability13.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.4931661259
DarkChem[M-H]-126.97731661259
AllCCS[M+H]+129.22832859911
AllCCS[M-H]-124.27532859911
DeepCCS[M+H]+124.59930932474
DeepCCS[M-H]-120.92730932474
DeepCCS[M-2H]-158.2430932474
DeepCCS[M+Na]+133.3930932474
AllCCS[M+H]+129.232859911
AllCCS[M+H-H2O]+124.632859911
AllCCS[M+NH4]+133.632859911
AllCCS[M+Na]+134.832859911
AllCCS[M-H]-124.332859911
AllCCS[M+Na-2H]-125.932859911
AllCCS[M+HCOO]-127.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
m-Aminobenzoic acidNC1=CC=CC(=C1)C(O)=O3273.6Standard polar33892256
m-Aminobenzoic acidNC1=CC=CC(=C1)C(O)=O1552.8Standard non polar33892256
m-Aminobenzoic acidNC1=CC=CC(=C1)C(O)=O1536.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
m-Aminobenzoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC(N)=C11595.7Semi standard non polar33892256
m-Aminobenzoic acid,1TMS,isomer #2C[Si](C)(C)NC1=CC=CC(C(=O)O)=C11725.4Semi standard non polar33892256
m-Aminobenzoic acid,2TMS,isomer #1C[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C)=C11725.9Semi standard non polar33892256
m-Aminobenzoic acid,2TMS,isomer #1C[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C)=C11750.8Standard non polar33892256
m-Aminobenzoic acid,2TMS,isomer #1C[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C)=C11829.2Standard polar33892256
m-Aminobenzoic acid,2TMS,isomer #2C[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C1770.1Semi standard non polar33892256
m-Aminobenzoic acid,2TMS,isomer #2C[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C1868.2Standard non polar33892256
m-Aminobenzoic acid,2TMS,isomer #2C[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C1954.8Standard polar33892256
m-Aminobenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C11725.6Semi standard non polar33892256
m-Aminobenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C11804.6Standard non polar33892256
m-Aminobenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC(N([Si](C)(C)C)[Si](C)(C)C)=C11763.3Standard polar33892256
m-Aminobenzoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC(N)=C11834.2Semi standard non polar33892256
m-Aminobenzoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=CC(C(=O)O)=C12013.1Semi standard non polar33892256
m-Aminobenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C12178.3Semi standard non polar33892256
m-Aminobenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C12154.6Standard non polar33892256
m-Aminobenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C12109.1Standard polar33892256
m-Aminobenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C(C)(C)C2240.3Semi standard non polar33892256
m-Aminobenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C(C)(C)C2240.1Standard non polar33892256
m-Aminobenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC(C(=O)O)=C1)[Si](C)(C)C(C)(C)C2125.2Standard polar33892256
m-Aminobenzoic acid,3TBDMS,isomer #1CC(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)=C12380.8Semi standard non polar33892256
m-Aminobenzoic acid,3TBDMS,isomer #1CC(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)=C12412.9Standard non polar33892256
m-Aminobenzoic acid,3TBDMS,isomer #1CC(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)=C12153.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - m-Aminobenzoic acid EI-B (Non-derivatized)splash10-000i-4900000000-e768f284b0ad9fa688a52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - m-Aminobenzoic acid EI-B (Non-derivatized)splash10-000i-4900000000-e768f284b0ad9fa688a52018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - m-Aminobenzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bi-6900000000-5055dc85abc93a87c6462017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - m-Aminobenzoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-3900000000-d96d075152745c6f5d232017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - m-Aminobenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - m-Aminobenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Aminobenzoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-3900000000-b6cb655f6ded12c673de2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Aminobenzoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-016r-9100000000-47171cdc0050a0ba58f32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Aminobenzoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-016r-9000000000-3d75db04ccdf6d696d3f2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Aminobenzoic acid LC-ESI-ITFT , positive-QTOFsplash10-000i-1900000000-b99ac73c3ae9561d99c92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Aminobenzoic acid 50V, Positive-QTOFsplash10-000i-1900000000-3539179dacc0af3e1b252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - m-Aminobenzoic acid 10V, Negative-QTOFsplash10-0006-9400000000-22a00bff4eaf264419f92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 10V, Positive-QTOFsplash10-000i-0900000000-caa9e00153a3a16122682017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 20V, Positive-QTOFsplash10-000i-2900000000-96b9acdf67eab6c3bf9c2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 40V, Positive-QTOFsplash10-014i-9100000000-f6bbcf082a3b9e2d43f72017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 10V, Negative-QTOFsplash10-000i-3900000000-2efea194138ca00e98d52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 20V, Negative-QTOFsplash10-000f-9500000000-d840735b2d7650a4af0c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 40V, Negative-QTOFsplash10-0006-9000000000-db71e4a65c0a6b2b2c082017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 10V, Negative-QTOFsplash10-000f-9800000000-0898c9a8e0c1ece2e4392021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 20V, Negative-QTOFsplash10-0006-9000000000-eef4c1f804c025cbb9782021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 40V, Negative-QTOFsplash10-0006-9000000000-172bdc125075867d5bcb2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 10V, Positive-QTOFsplash10-000i-3900000000-2aad2dc63caed09f95d92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 20V, Positive-QTOFsplash10-006x-8900000000-724130510a7832c96f382021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - m-Aminobenzoic acid 40V, Positive-QTOFsplash10-0fr6-9000000000-8812b1e7f3cb93067efa2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified0.07 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02054
Phenol Explorer Compound IDNot Available
FooDB IDFDB022725
KNApSAcK IDNot Available
Chemspider ID7141
KEGG Compound IDNot Available
BioCyc IDHMDB01891
BiGG IDNot Available
Wikipedia Link3-Aminobenzoic_acid
METLIN ID6374
PubChem Compound7419
PDB IDNot Available
ChEBI ID42682
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1187341
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]