Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110108
Identification
Name: anthranilate
Description:An aminobenzoate that is the conjugate base of anthranilic acid, obtained by deprotonation of the carboxy group.
Structure
Thumb
Synonyms:
  • anthranilic acid
  • 2-aminobenzoic acid
  • vitamin L1
  • o-aminobenzoic acid
  • 2-aminobenzoate
  • o-aminobenzoate
Chemical Formula: C7H6NO2
Average Molecular Weight: 136.13
Monoisotopic Molecular Weight: 137.0476784741
InChI Key: RWZYAGGXGHYGMB-UHFFFAOYSA-M
InChI: InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)/p-1
CAS number: 118-92-3
IUPAC Name:2-aminobenzoate
Traditional IUPAC Name: 2-aminobenzoic acid
SMILES:C(C1(C(=CC=CC=1)N))(=O)[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassBenzenoids
Class Benzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parent Aminobenzoic 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 Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 146.5 °C
Experimental Properties:
PropertyValueReference
Melting Point146.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.5 mg/mLNot Available
LogP1.21HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility6.81 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m3·mol-1ChemAxon
Polarizability13.29 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-014i-1950000000-5595652a2e8f93679437View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014i-1960000000-889ed538406d5aa57a5dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00xr-9650000000-e0611721f0bf7b5bb2f8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00r6-2910000000-0daf33fe6231b5e15b0eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-3970000000-3351c7d8036c42c4cd41View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00kf-9400000000-395d42e11895b80f4e9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-8c390367e035aea8527aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-899b596a227cd9a1769dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-3cc9be013399e30d7eaeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-655ef8fc722e0b1b6d14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-4d0520217d12a10f9273View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-bab8539624c8af4e6434View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-f51f2db6bf1da2e26d20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-86d698a8c81a3e765840View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-6df94712ad580bebfd21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9100000000-a1ce64280c2d7f3b85dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-454f848122c778e951adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-7de473c1ca6bf702b2acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-94f19baa1ae36f43be60View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-2900000000-c2bbbe5e00434e635ad2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-4900000000-f8f84a5536375300afbdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00r6-9200000000-fccd86d3a0a4bfe2e5d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-9000000000-91ceb340e5cf91473cbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-80972c552b97ae764bc4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-f494672ce9de4818b8c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9300000000-9bbb2f00817538e072d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-e7e07e78dd5baa5c3f87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-54a3d793d6fbf0220b47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-9200000000-bd780d6ca957af006488View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-9800000000-93111d593c96a3298a6cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-014u-9600000000-5b8e271f29d04a87c89aView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Igari T, Tsuchizawa M, Shimamura T: Alteration of tryptophan metabolism in the synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Tohoku J Exp Med. 1987 Oct;153(2):79-86. [3500530 ]
  • Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [1244085 ]
  • Di Marco GS, Quinto BM, Juliano M, Carmona AK, Stella RC, Plavnik FL, Casarini DE: Purification and characterization of a neutral endopeptidase-like enzyme from human urine. J Hypertens. 1998 Dec;16(12 Pt 2):1971-8. [9886885 ]
  • Hagag N, Birnbaum ER, Darnall DW: Resonance energy transfer between cysteine-34, tryptophan-214, and tyrosine-411 of human serum albumin. Biochemistry. 1983 May 10;22(10):2420-7. [6860638 ]
  • Little CH, Georgiou GM, Shelton MJ, Simpson F, Cone RE: Clinical and immunological responses in subjects sensitive to solvents. Arch Environ Health. 1999 Jan-Feb;54(1):6-14. [10025410 ]
  • Ritchie MR, Morton MS, Thompson AM, Deighton N, Blake A, Cummings JH, Steel CM: Investigation of the reliability of 24 h urine excretion as a biomarker of isoflavone exposure over time and over a wide range of isoflavone intakes. Eur J Clin Nutr. 2004 Sep;58(9):1286-9. [15054404 ]
  • Ortega RM, Andres P, Martinez RM, Lopez-Sobaler AM: Vitamin A status during the third trimester of pregnancy in Spanish women: influence on concentrations of vitamin A in breast milk. Am J Clin Nutr. 1997 Sep;66(3):564-8. [9280174 ]
  • Alves MF, Araujo MC, Juliano MA, Oliveira EM, Krieger JE, Casarini DE, Juliano L, Carmona AK: A continuous fluorescent assay for the determination of plasma and tissue angiotensin I-converting enzyme activity. Braz J Med Biol Res. 2005 Jun;38(6):861-8. Epub 2005 Jun 1. [15933779 ]
  • Soma J, Sugawara T, Huang YD, Nakajima J, Kawamura M: Tranilast slows the progression of advanced diabetic nephropathy. Nephron. 2002;92(3):693-8. [12372957 ]
  • Ahmad S: The functional roles of cytochrome P-450 mediated systems: present knowledge and future areas of investigations. Drug Metab Rev. 1979;10(1):1-14. [118858 ]
  • Spivak W, Carey MC: Reverse-phase h.p.l.c. separation, quantification and preparation of bilirubin and its conjugates from native bile. Quantitative analysis of the intact tetrapyrroles based on h.p.l.c. of their ethyl anthranilate azo derivatives. Biochem J. 1985 Feb 1;225(3):787-805. [3919713 ]
Synthesis Reference: Wang, Chengyin; Yang, Jisheng; Wang, Honghai. Production of o-aminobenzoic acid from by-product o-nitrobenzoic acid. Huaxue Shijie (1999), 40(5), 274-277.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS118-92-3
ChEBI16567
ChemSpider4573598
HMDBHMDB01123
IAF126033883
KEGGC00108
MetaboLightsMTBLC16567
PubChem5459842