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Identification |
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YMDB ID | YMDB00278 |
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Name | 2-Aminobenzoic acid |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | 2-Aminobenzoic acid, also known as vitamin L1 or 2-aminobenzoate, 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 through the action of the enzyme anthranilate synthase component. In addition, 2-aminobenzoic acid and phosphoribosyl pyrophosphate can be converted into N-(5-phosphoribosyl)-anthranilate through its interaction with 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. |
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Structure | |
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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
- H-2-Abz-OH
- Anthranilic acid, calcium (2:1) salt
- Anthranilic acid, cadmium salt
- Anthranilic acid, dihydrochloride
- Anthranilic acid, monosodium salt
- Anthranilic acid, monolithium salt
- Anthranilic acid, hydrochloride
- Sodium anthranilate
- (CH3)3NO
- Me3n(+)O(-)
- Me3n(O)
- N(CH3)3O
- TMAO
- Trimethylamine oxide
- Trimethylaminoxid
- Trimethyloxamine
- N,N-Dimethylmethanamine N-oxide
- TMA-oxide
- Trimethylamine-N-oxide
- Triox
- Trimethylammonium oxide
- 3-Pyridinecarboxamide
- beta-Pyridinecarboxamide
- Niacin
- Nicotinamid
- Nicotinic acid amide
- Nicotinsaeureamid
- Nikotinamid
- Nikotinsaeureamid
- Vitamin b3
- Vitamin PP
- Nicotinamide
- b-Pyridinecarboxamide
- Β-pyridinecarboxamide
- Nicotinate amide
- 3-Carbamoylpyridine
- 3-Pyridinecarboxylic acid amide
- Acid amide
- Amid kyseliny nikotinove
- Amide PP
- Aminicotin
- Amixicotyn
- Amnicotin
- Austrovit PP
- Benicot
- Delonin amide
- Dipegyl
- Dipigyl
- Endobion
- Factor PP
- Hansamid
- Inovitan PP
- m-(Aminocarbonyl)pyridine
- Mediatric
- NAM
- Nandervit-N
- Niacevit
- Niamide
- Niavit PP
- Nicamide
- Nicamina
- Nicamindon
- Nicasir
- Nicobion
- Nicofort
- Nicogen
- Nicomidol
- Nicosan 2
- Nicosylamide
- Nicota
- Nicotamide
- Nicotilamide
- Nicotililamido
- Nicotinamida
- Nicotinamidum
- Nicotine acid amide
- Nicotine amide
- Nicotinic amide
- Nicotinsaureamid
- Nicotol
- Nicotylamide
- Nicotylamidum
- Nicovel
- Nicovit
- Nicovitina
- Nicovitol
- Nicozymin
- Nictoamide
- Niko-tamin
- Niocinamide
- Niozymin
- Papulex
- Pelmin
- Pelmine
- Pelonin amide
- PP-Faktor
- Propamine a
- Pyridine-3-carboxylic acid amide
- Savacotyl
- Vi-nicotyl
- Vi-noctyl
- Witamina PP
- 3 Pyridinecarboxamide
- Astra brand OF niacinamide
- b 3, Vitamin
- Niacinamide merck brand
- Pharmagenix brand OF niacinamide
- b3, Vitamin
- Enduramide
- Jenapharm, nicotinsäureamid
- Niacinamide jenapharm brand
- Niacinamide pharmagenix brand
- Jenapharm brand OF niacinamide
- Nicotinsäureamid jenapharm
- Vitamin b 3
- Merck brand OF niacinamide
- Niacinamide astra brand
- HCONHCH3
- Methylformamide
- Monomethylformamide
- N-Methyl-formamide
- N-Monomethylformamide
- NMF
- (+-)-1'-Demethyl-nicotine
- (+-)-1'-Demethylnicotine
- (+-)-3-(2-Pyrrolidinyl)pyridine
- (+-)-Nornicotine
- (R)-3-(Pyrrolidin-2-yl)pyridine
- (R,S)-Nornicotine
- (S)-2-(3-Pyridyl)pyrrolidine
- 2-(3-Pyridyl)pyrrolidine
- 3-(2-Pyrrolidinyl)pyridine
- DL-Norcitine
- L-Nor-nicotine
- Nornicotin
- S-(-)-Nornicotine
- Nornicotine tartrate, (S)-(R-(r*,r*))-isomer
- Nornicotine, (R)-isomer
- Nornicotine, (S)-isomer
- 2-(Acetylamino)-2-deoxy-6-O-phosphono-alpha-D-mannopyranose
- 2-Acetamido-2-deoxy-6-O-phosphono-alpha-D-mannopyranose
- 2-Acetamido-2-deoxy-6-O-phosphono-alpha-D-mannose
- 2-(Acetylamino)-2-deoxy-6-O-phosphono-a-D-mannopyranose
- 2-(Acetylamino)-2-deoxy-6-O-phosphono-α-D-mannopyranose
- 2-Acetamido-2-deoxy-6-O-phosphono-a-D-mannopyranose
- 2-Acetamido-2-deoxy-6-O-phosphono-α-D-mannopyranose
- 2-Acetamido-2-deoxy-6-O-phosphono-a-D-mannose
- 2-Acetamido-2-deoxy-6-O-phosphono-α-D-mannose
- N-Acetyl-D-mannosamine 6-phosphoric acid
- ManNAc-6-p
- N-Acetyl-D-mannosamine-6-p
- N-Acetyl-D-mannosamine-6-phosphate
- N-Acetylmannosamine-6-p
- 2-Acetamido-2-deoxy-mannose-6-phosphate
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CAS number | 118-92-3 |
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Weight | Average: 137.136 Monoisotopic: 137.047678473 |
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InChI Key | RWZYAGGXGHYGMB-UHFFFAOYSA-N |
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InChI | InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10) |
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IUPAC Name | 2-aminobenzoic acid |
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Traditional IUPAC Name | 2-aminobenzoic acid |
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Chemical Formula | C7H7NO2 |
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SMILES | [H]OC(=O)C1=C([H])C([H])=C([H])C([H])=C1N([H])[H] |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | Aminobenzoic acids |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | 146.5 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | 3.5 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | LogP | 1.21 [HANSCH,C ET AL. (1995)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways | Phenylalanine, tyrosine and tryptophan biosynthesis | ec00400 |  | Tryptophan metabolism | ec00380 |  |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-014i-1950000000-5595652a2e8f93679437 | JSpectraViewer | 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 | JSpectraViewer | 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 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-00r6-2910000000-0daf33fe6231b5e15b0e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-014i-3970000000-3351c7d8036c42c4cd41 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00kf-9400000000-b65ee27505e8c4bcca28 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-014i-0490000000-4165d1d7b8fff53889dd | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-1950000000-5595652a2e8f93679437 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-1960000000-889ed538406d5aa57a5d | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00xr-9650000000-e0611721f0bf7b5bb2f8 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00r6-2910000000-0daf33fe6231b5e15b0e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014i-3970000000-3351c7d8036c42c4cd41 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00kr-7900000000-a9c510a71b30a8fcc1b8 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-7900000000-cb7be965685a5ee30fbd | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-00kf-9400000000-395d42e11895b80f4e9c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-8c390367e035aea8527a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0006-9000000000-899b596a227cd9a1769d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0900000000-3cc9be013399e30d7eae | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0900000000-655ef8fc722e0b1b6d14 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-4d0520217d12a10f9273 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0006-9000000000-bab8539624c8af4e6434 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0900000000-f51f2db6bf1da2e26d20 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0900000000-86d698a8c81a3e765840 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-000i-0900000000-6df94712ad580bebfd21 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0006-9100000000-a1ce64280c2d7f3b85df | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0006-9000000000-454f848122c778e951ad | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0006-9000000000-7de473c1ca6bf702b2ac | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-94f19baa1ae36f43be60 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-00di-2900000000-c2bbbe5e00434e635ad2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-4900000000-f8f84a5536375300afbd | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00r6-9200000000-fccd86d3a0a4bfe2e5d7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-014i-9000000000-91ceb340e5cf91473cba | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-014i-9000000000-80972c552b97ae764bc4 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00di-4900000000-f494672ce9de4818b8c5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0006-9300000000-9bbb2f00817538e072d5 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0079-0900000000-e7e07e78dd5baa5c3f87 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-1900000000-54a3d793d6fbf0220b47 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0umi-9200000000-bd780d6ca957af006488 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000f-9800000000-93111d593c96a3298a6c | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-014u-9600000000-5b8e271f29d04a87c89a | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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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
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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. |
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