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Anthranilic acid (FDB000896)

Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2020-09-17 15:38:48 UTC
Primary IDFDB000896
Secondary Accession Numbers
  • FDB030679
Chemical Information
FooDB NameAnthranilic acid
Description2-Aminobenzoic acid, also known as anthranilate or anthranilic 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. An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. 2-Aminobenzoic acid is a moderately basic compound (based on its pKa). 2-Aminobenzoic acid exists in all living species, ranging from bacteria to humans. Within humans, 2-aminobenzoic acid participates in a number of enzymatic reactions. In particular, 2-aminobenzoic acid and formic acid can be biosynthesized from formylanthranilic acid through the action of the enzyme kynurenine formamidase. In addition, 2-aminobenzoic acid and L-alanine can be biosynthesized from L-kynurenine through its interaction with the enzyme kynureninase. In humans, 2-aminobenzoic acid is involved in tryptophan metabolism. Outside of the human body, 2-Aminobenzoic acid has been detected, but not quantified in, several different foods, such as mexican groundcherries, caraway, cinnamons, sugar apples, and strawberry guava. This could make 2-aminobenzoic acid a potential biomarker for the consumption of these foods. 2-Aminobenzoic acid is a potentially toxic compound.
CAS Number118-92-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.81 g/LALOGPS
logP0.78ALOGPS
logP1.45ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)1.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m³·mol⁻¹ChemAxon
Polarizability13.29 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H7NO2
IUPAC name2-aminobenzoic acid
InChI IdentifierInChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
InChI KeyRWZYAGGXGHYGMB-UHFFFAOYSA-N
Isomeric SMILESNC1=CC=CC=C1C(O)=O
Average Molecular Weight137.136
Monoisotopic Molecular Weight137.047678473
Classification
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
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 61.31%; H 5.14%; N 10.21%; O 23.33%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data335 (e 4700) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014u-9600000000-5b8e271f29d04a87c89a2014-09-20View Spectrum
GC-MSAnthranilic acid, 2 TMS, GC-MS Spectrumsplash10-014i-1950000000-5595652a2e8f93679437Spectrum
GC-MSAnthranilic acid, non-derivatized, GC-MS Spectrumsplash10-014i-1960000000-889ed538406d5aa57a5dSpectrum
GC-MSAnthranilic acid, 2 TMS, GC-MS Spectrumsplash10-00xr-9650000000-e0611721f0bf7b5bb2f8Spectrum
GC-MSAnthranilic acid, 1 TMS, GC-MS Spectrumsplash10-00r6-2910000000-0daf33fe6231b5e15b0eSpectrum
GC-MSAnthranilic acid, 2 TMS, GC-MS Spectrumsplash10-014i-3970000000-3351c7d8036c42c4cd41Spectrum
GC-MSAnthranilic acid, non-derivatized, GC-MS Spectrumsplash10-00kf-9400000000-b65ee27505e8c4bcca28Spectrum
GC-MSAnthranilic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0490000000-4165d1d7b8fff53889ddSpectrum
GC-MSAnthranilic acid, non-derivatized, GC-MS Spectrumsplash10-014i-1950000000-5595652a2e8f93679437Spectrum
GC-MSAnthranilic acid, non-derivatized, GC-MS Spectrumsplash10-014i-1960000000-889ed538406d5aa57a5dSpectrum
GC-MSAnthranilic acid, non-derivatized, GC-MS Spectrumsplash10-00xr-9650000000-e0611721f0bf7b5bb2f8Spectrum
GC-MSAnthranilic acid, non-derivatized, GC-MS Spectrumsplash10-00r6-2910000000-0daf33fe6231b5e15b0eSpectrum
GC-MSAnthranilic acid, non-derivatized, GC-MS Spectrumsplash10-014i-3970000000-3351c7d8036c42c4cd41Spectrum
Predicted GC-MSAnthranilic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kr-7900000000-a9c510a71b30a8fcc1b8Spectrum
Predicted GC-MSAnthranilic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-7900000000-cb7be965685a5ee30fbdSpectrum
Predicted GC-MSAnthranilic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAnthranilic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00kf-9400000000-395d42e11895b80f4e9c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-8c390367e035aea8527a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-899b596a227cd9a1769d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-3cc9be013399e30d7eae2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-655ef8fc722e0b1b6d142012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-4d0520217d12a10f92732012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-bab8539624c8af4e64342012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-f51f2db6bf1da2e26d202012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-86d698a8c81a3e7658402012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-6df94712ad580bebfd212012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9100000000-a1ce64280c2d7f3b85df2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-454f848122c778e951ad2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-7de473c1ca6bf702b2ac2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-94f19baa1ae36f43be602012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-2900000000-c2bbbe5e00434e635ad22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-4900000000-f8f84a5536375300afbd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00r6-9200000000-fccd86d3a0a4bfe2e5d72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-9000000000-91ceb340e5cf91473cba2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-80972c552b97ae764bc42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-f494672ce9de4818b8c52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9300000000-9bbb2f00817538e072d52012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-e7e07e78dd5baa5c3f872015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-54a3d793d6fbf0220b472015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-9200000000-bd780d6ca957af0064882015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-9800000000-93111d593c96a3298a6c2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID222
ChEMBL IDCHEMBL14173
KEGG Compound IDC00108
Pubchem Compound ID227
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB04166
HMDB IDHMDB01123
CRC / DFC (Dictionary of Food Compounds) IDBLS86-X:BLS86-X
EAFUS IDNot Available
Dr. Duke IDANTHRANILIC-ACID
BIGG ID33883
KNApSAcK IDNot Available
HET IDBE2
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti feedantDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
insulinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
insulinotonicDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).