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Record Information
Version	2.0
Creation Date	2012-05-31 13:45:41 -0600
Update Date	2015-09-13 12:56:10 -0600
Secondary Accession Numbers	ECMDB01123
Identification
Name:	2-Aminobenzoic acid
Description	2-Aminobenzoic acid is an organic compound. It is a substrate of enzyme anthranilate hydroxylase [EC 1.14.13.35] in benzoate degradation via hydroxylation pathway (KEGG).
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa3a4bb60> Close
Synonyms:	1-Amino-2-carboxybenzene 2-Amino-Benzoate 2-Amino-Benzoic acid 2-Aminobenzoate 2-Aminobenzoic acid 2-Aminophenylacetate 2-Aminophenylacetic acid 2-Carboxyaniline Anthranate Anthranic acid Anthranilate Anthranilate gr Anthranilic acid Anthranilic acid gr Carboxyaniline H-2-Abz-OH 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
Chemical Formula:	C7H7NO2
Weight:	Average: 137.136 Monoisotopic: 137.047678473
InChI Key:	RWZYAGGXGHYGMB-UHFFFAOYSA-N
InChI:	InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
CAS number:	118-92-3
IUPAC Name:	2-aminobenzoic acid
Traditional IUPAC Name:	2-aminobenzoic acid
SMILES:	NC1=CC=CC=C1C(O)=O
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	Benzoic acids Benzoyl derivatives Aniline and substituted anilines Vinylogous amides Amino acids Monocarboxylic acids and derivatives Carboxylic acids Primary amines Organopnictogen compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
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	aminobenzoic acid (CHEBI:30754 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	146.5 °C
Experimental Properties:	Property Value Source Water Solubility: 3.5 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] PhysProp LogP: 1.21 [HANSCH,C ET AL. (1995)] PhysProp
Predicted Properties	Property Value Source Water Solubility 6.81 g/L ALOGPS logP 0.78 ALOGPS logP 1.45 ChemAxon logS -1.3 ALOGPS pKa (Strongest Acidic) 4.89 ChemAxon pKa (Strongest Basic) 1.95 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 63.32 Ų ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 38.01 m³·mol⁻¹ ChemAxon Polarizability 13.29 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Chorismate + L-Glutamine <> 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acid 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + N-(5-Phospho-D-ribosyl)anthranilate Acetyl-CoA + 2-Aminobenzoic acid > N-Acetylanthranilate + Coenzyme A Chorismate + Ammonia <> 2-Aminobenzoic acid + Pyruvic acid + Water Chorismate + L-Glutamine <> 2-Aminobenzoic acid + Pyruvic acid + L-Glutamate N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate <> 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate Chorismate + L-Glutamine > Hydrogen ion + 2-Aminobenzoic acid + Pyruvic acid + L-Glutamate N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate < 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate Hydrogen ion + methyl red + NADH 2-Aminobenzoic acid + N,N'-dimethyl-p-phenylenediamine + NAD Chorismate + L-Glutamine > 2-Aminobenzoic acid + Pyruvic acid + L-Glutamate N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate > 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate Chorismate + L-Glutamine > L-Glutamic acid + Pyruvic acid + Hydrogen ion + 2-Aminobenzoic acid + L-Glutamate 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate Chorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acid Chorismate + Ammonia <>2 2-Aminobenzoic acid + Pyruvic acid + Water Chorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acid Chorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acid
SMPDB Pathways:	Tryptophan metabolism PW000815 tryptophan metabolism II PW001916
KEGG Pathways:	1,4-Dichlorobenzene degradation ec00627 Biphenyl degradation ec00621 Metabolic pathways eco01100 Microbial metabolism in diverse environments ec01120 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Tryptophan metabolism ec00380
EcoCyc Pathways:	tryptophan biosynthesis TRPSYN-PWY
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 3± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 3± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 3± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 5± 0 uM BW25113 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Stationary Phase, glucose limited Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 37 oC PMID: 17379776 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) splash10-014i-1950000000-5595652a2e8f93679437 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-014i-1960000000-889ed538406d5aa57a5d View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) splash10-00xr-9650000000-e0611721f0bf7b5bb2f8 View in MoNA GC-MS GC-MS Spectrum - GC-MS (1 TMS) splash10-00r6-2910000000-0daf33fe6231b5e15b0e View in MoNA GC-MS GC-MS Spectrum - GC-MS (2 TMS) splash10-014i-3970000000-3351c7d8036c42c4cd41 View in MoNA GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-00kf-9400000000-b65ee27505e8c4bcca28 View in MoNA GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-014i-0490000000-4165d1d7b8fff53889dd View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014i-1950000000-5595652a2e8f93679437 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014i-1960000000-889ed538406d5aa57a5d View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00xr-9650000000-e0611721f0bf7b5bb2f8 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-00r6-2910000000-0daf33fe6231b5e15b0e View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-014i-3970000000-3351c7d8036c42c4cd41 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-00kr-7900000000-a9c510a71b30a8fcc1b8 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-00di-7900000000-cb7be965685a5ee30fbd View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive splash10-00kf-9400000000-395d42e11895b80f4e9c View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-000i-0900000000-8c390367e035aea8527a View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0006-9000000000-899b596a227cd9a1769d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-014i-0900000000-3cc9be013399e30d7eae View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-00di-0900000000-655ef8fc722e0b1b6d14 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-000i-0900000000-4d0520217d12a10f9273 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0006-9000000000-bab8539624c8af4e6434 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-014i-0900000000-f51f2db6bf1da2e26d20 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-00di-0900000000-86d698a8c81a3e765840 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative splash10-000i-0900000000-6df94712ad580bebfd21 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative splash10-0006-9100000000-a1ce64280c2d7f3b85df View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative splash10-0006-9000000000-454f848122c778e951ad View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative splash10-0006-9000000000-7de473c1ca6bf702b2ac View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative splash10-0006-9000000000-94f19baa1ae36f43be60 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive splash10-00di-2900000000-c2bbbe5e00434e635ad2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive splash10-00di-4900000000-f8f84a5536375300afbd View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive splash10-00r6-9200000000-fccd86d3a0a4bfe2e5d7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive splash10-014i-9000000000-91ceb340e5cf91473cba View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive splash10-014i-9000000000-80972c552b97ae764bc4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-00di-4900000000-f494672ce9de4818b8c5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-0006-9300000000-9bbb2f00817538e072d5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0079-0900000000-e7e07e78dd5baa5c3f87 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00di-1900000000-54a3d793d6fbf0220b47 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0umi-9200000000-bd780d6ca957af006488 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000f-9800000000-93111d593c96a3298a6c View in MoNA MS Mass Spectrum (Electron Ionization) splash10-014u-9600000000-5b8e271f29d04a87c89a View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,1H] 2D NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	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. Pubmed: 118858 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. Pubmed: 15933779 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621 Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. Pubmed: 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. Pubmed: 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. Pubmed: 6860638 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. Pubmed: 3500530 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 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. Pubmed: 10025410 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. Pubmed: 9280174 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. Pubmed: 15054404 Soma J, Sugawara T, Huang YD, Nakajima J, Kawamura M: Tranilast slows the progression of advanced diabetic nephropathy. Nephron. 2002;92(3):693-8. Pubmed: 12372957 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. Pubmed: 3919713 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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)
Links
External Links:	Resource Link CHEBI ID 30754 HMDB ID HMDB01123 Pubchem Compound ID 227 Kegg ID C00108 ChemSpider ID 222 Wikipedia Anthranilic acid BioCyc ID ANTHRANILATE EcoCyc ID ANTHRANILATE Ligand Expo BE2

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