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2-Aminobenzoic acid (YMDB00278)

Identification
YMDB IDYMDB00278
Name2-Aminobenzoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Aminobenzoic acid, also known as anthranilate or vitamin L1, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. 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 yeast, 2-aminobenzoic acid participates in a number of enzymatic reactions. In particular, pyruvic acid, L-glutamic acid, and 2-aminobenzoic acid can be biosynthesized from chorismate and L-glutamine; which is catalyzed by the enzyme anthranilate synthase component. In addition, 2-aminobenzoic acid and phosphoribosyl pyrophosphate can be converted into N-(5-phosphoribosyl)-anthranilate through the action of the enzyme anthranilate phosphoribosyltransferase. In yeast, 2-aminobenzoic acid is involved in the metabolic pathway called the tryptophan metabolism pathway. 2-Aminobenzoic acid is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 1-Amino-2-carboxybenzene
  • 2-amino-Benzoate
  • 2-amino-Benzoic acid
  • 2-Aminobenzoate
  • 2-Aminobenzoic acid
  • 2-Aminophenylacetate
  • 2-Aminophenylacetic acid
  • 2-Carboxyaniline
  • Aminobenzoic acid
  • Anthranate
  • Anthranic acid
  • Anthranilate
  • Anthranilic acid
  • anthranilic acid gr
  • Benzoic acid, 2-amino-
  • Benzoic acid, o-amino-
  • Carboxyaniline
  • Kyselina anthranilova
  • Kyselina o-aminobenzoova
  • o-amino-Benzoate
  • o-amino-Benzoic acid
  • o-Aminobenzoate
  • o-Aminobenzoic acid
  • o-Anthranilate
  • o-Anthranilic acid
  • o-Carboxyaniline
  • Ortho-amidobenzoate
  • Ortho-amidobenzoic acid
  • Ortho-aminobenzoate
  • Ortho-aminobenzoic acid
  • Vitamin L
  • Vitamin L1
  • 2-Aminobenzoesaeure
  • O-Aminobenzoesaeure
  • Anthranilic acid, cadmium salt
  • Anthranilic acid, calcium (2:1) salt
  • Anthranilic acid, monolithium salt
  • Sodium anthranilate
  • Anthranilic acid, dihydrochloride
  • Anthranilic acid, hydrochloride
  • Anthranilic acid, monosodium salt
  • H-2-Abz-OH
CAS number118-92-3
WeightAverage: 137.136
Monoisotopic: 137.047678473
InChI KeyRWZYAGGXGHYGMB-UHFFFAOYSA-N
InChIInChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
IUPAC Name2-aminobenzoic acid
Traditional IUPAC Name2-aminobenzoic acid
Chemical FormulaC7H7NO2
SMILES[H]OC(=O)C1=C([H])C([H])=C([H])C([H])=C1N([H])[H]
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
  • 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
Physical Properties
StateSolid
Charge0
Melting point146.5 °C
Experimental Properties
PropertyValueReference
Water Solubility3.5 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP1.21 [HANSCH,C ET AL. (1995)]PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
Tryptophan metabolismec00380 Map00380
SMPDB Reactions
L-Kynurenine + water → hydron + L-Alanine + 2-Aminobenzoic acid
Chorismate + L-Glutamine → Pyruvic acid + L-Glutamic acid + hydron + 2-Aminobenzoic acid
2-Aminobenzoic acid + Phosphoribosyl pyrophosphate → Pyrophosphate + N-(5-Phosphonato-beta-D-ribosyl)anthranilate
KEGG Reactions
2-Aminobenzoic acid + Phosphoribosyl pyrophosphate → Pyrophosphate + N-(5-phospho-beta-D-ribosyl)anthranilic acid
Chorismate + L-Glutamine → 2-Aminobenzoic acid + Pyruvic acid + L-Glutamic acid + hydron
L-Kynurenine + water → 2-Aminobenzoic acid + L-Alanine + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-014i-1950000000-5595652a2e8f93679437JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-1960000000-889ed538406d5aa57a5dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00xr-9650000000-e0611721f0bf7b5bb2f8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00r6-2910000000-0daf33fe6231b5e15b0eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-3970000000-3351c7d8036c42c4cd41JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9400000000-b65ee27505e8c4bcca28JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0490000000-4165d1d7b8fff53889ddJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1950000000-5595652a2e8f93679437JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1960000000-889ed538406d5aa57a5dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xr-9650000000-e0611721f0bf7b5bb2f8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00r6-2910000000-0daf33fe6231b5e15b0eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-3970000000-3351c7d8036c42c4cd41JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-7900000000-a9c510a71b30a8fcc1b8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7900000000-cb7be965685a5ee30fbdJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00kf-9400000000-395d42e11895b80f4e9cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-8c390367e035aea8527aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-899b596a227cd9a1769dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-3cc9be013399e30d7eaeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-655ef8fc722e0b1b6d14JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-4d0520217d12a10f9273JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-bab8539624c8af4e6434JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-f51f2db6bf1da2e26d20JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-86d698a8c81a3e765840JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-6df94712ad580bebfd21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9100000000-a1ce64280c2d7f3b85dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-454f848122c778e951adJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-7de473c1ca6bf702b2acJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-94f19baa1ae36f43be60JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-2900000000-c2bbbe5e00434e635ad2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-4900000000-f8f84a5536375300afbdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00r6-9200000000-fccd86d3a0a4bfe2e5d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-9000000000-91ceb340e5cf91473cbaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-80972c552b97ae764bc4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4900000000-f494672ce9de4818b8c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9300000000-9bbb2f00817538e072d5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-e7e07e78dd5baa5c3f87JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-54a3d793d6fbf0220b47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-9200000000-bd780d6ca957af006488JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-9800000000-93111d593c96a3298a6cJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-014u-9600000000-5b8e271f29d04a87c89aJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Crombie, T., Boyle, J. P., Coggins, J. R., Brown, A. J. (1994). "The folding of the bifunctional TRP3 protein in yeast is influenced by a translational pause which lies in a region of structural divergence with Escherichia coli indoleglycerol-phosphate synthase." Eur J Biochem 226:657-664.8001582
  • Panozzo, C., Nawara, M., Suski, C., Kucharczyka, R., Skoneczny, M., Becam, A. M., Rytka, J., Herbert, C. J. (2002). "Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae." FEBS Lett 517:97-102.12062417
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.
External Links:
ResourceLink
CHEBI ID30754
HMDB IDHMDB01123
Pubchem Compound ID227
Kegg IDC00108
ChemSpider ID222
FOODB IDFDB000896
WikipediaAnthranilic_acid
BioCyc IDANTHRANILATE

Enzymes

Protein Details
1. Anthranilate synthase component 2
General function:
Involved in catalytic activity
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
TRP3
Uniprot ID:
P00937
Molecular weight:
53488.89844
Reactions
Chorismate + L-glutamine → anthranilate + pyruvate + L-glutamate.
1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate → 1-C-(3-indolyl)-glycerol 3-phosphate + CO(2) + H(2)O.
Protein Details
2. Anthranilate synthase component 1
General function:
Involved in biosynthetic process
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
TRP2
Uniprot ID:
P00899
Molecular weight:
56767.0
Reactions
Chorismate + L-glutamine → anthranilate + pyruvate + L-glutamate.
Protein Details
3. Anthranilate phosphoribosyltransferase
General function:
Involved in anthranilate phosphoribosyltransferase activity
Specific function:
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1- diphosphate
Gene Name:
TRP4
Uniprot ID:
P07285
Molecular weight:
41374.0
Reactions
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate → anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.
Protein Details
4. Kynureninase
General function:
Involved in metabolic process
Specific function:
Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3- hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3- hydroxyanthranilic acid (3-OHAA), respectively
Gene Name:
BNA5
Uniprot ID:
Q05979
Molecular weight:
51031.60156
Reactions
L-kynurenine + H(2)O → anthranilate + L-alanine.
L-3-hydroxykynurenine + H(2)O → 3-hydroxyanthranilate + L-alanine.
Protein Details
5. Probable kynurenine formamidase
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L- kynurenine, the second step in the conversion of tryptophan to nicotinic acid, NAD(H) and NADP(H)
Gene Name:
BNA7
Uniprot ID:
Q04066
Molecular weight:
29991.0
Reactions
N-formyl-L-kynurenine + H(2)O → formate + L-kynurenine.