Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB110108 |
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Identification |
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Name: |
anthranilate |
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Description: | An aminobenzoate that is the conjugate base of anthranilic acid, obtained by deprotonation of the carboxy group. |
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Structure |
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Synonyms: | -
anthranilic acid
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2-aminobenzoic acid
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vitamin L1
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o-aminobenzoic acid
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2-aminobenzoate
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o-aminobenzoate
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Chemical Formula: |
C7H6NO2
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Average Molecular Weight: |
136.13 |
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Monoisotopic Molecular
Weight: |
137.0476784741 |
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InChI Key: |
RWZYAGGXGHYGMB-UHFFFAOYSA-M |
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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)/p-1 |
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CAS
number: |
118-92-3 |
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IUPAC Name: | 2-aminobenzoate |
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Traditional IUPAC Name: |
2-aminobenzoic acid |
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SMILES: | C(C1(C(=CC=CC=1)N))(=O)[O-] |
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Chemical Taxonomy |
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Taxonomy Description | This 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. |
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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: | -1 |
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Melting point: |
146.5 °C |
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Experimental Properties: |
Property | Value | Reference |
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Melting Point | 146.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 3.5 mg/mL | Not Available | LogP | 1.21 | HANSCH,C ET AL. (1995) |
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Predicted Properties |
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Biological Properties |
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Cellular Locations: |
Not Available |
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Reactions: | |
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Pathways: |
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Spectra |
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Spectra: |
Spectrum Type | Description | Splash Key | |
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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 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | splash10-014i-1960000000-889ed538406d5aa57a5d | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00xr-9650000000-e0611721f0bf7b5bb2f8 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-00r6-2910000000-0daf33fe6231b5e15b0e | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-014i-3970000000-3351c7d8036c42c4cd41 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS | Not Available |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-00kf-9400000000-395d42e11895b80f4e9c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-8c390367e035aea8527a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0006-9000000000-899b596a227cd9a1769d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0900000000-3cc9be013399e30d7eae | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0900000000-655ef8fc722e0b1b6d14 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-4d0520217d12a10f9273 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0006-9000000000-bab8539624c8af4e6434 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0900000000-f51f2db6bf1da2e26d20 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0900000000-86d698a8c81a3e765840 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-000i-0900000000-6df94712ad580bebfd21 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0006-9100000000-a1ce64280c2d7f3b85df | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0006-9000000000-454f848122c778e951ad | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0006-9000000000-7de473c1ca6bf702b2ac | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-94f19baa1ae36f43be60 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-00di-2900000000-c2bbbe5e00434e635ad2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-4900000000-f8f84a5536375300afbd | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00r6-9200000000-fccd86d3a0a4bfe2e5d7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-014i-9000000000-91ceb340e5cf91473cba | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-014i-9000000000-80972c552b97ae764bc4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00di-4900000000-f494672ce9de4818b8c5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0006-9300000000-9bbb2f00817538e072d5 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0079-0900000000-e7e07e78dd5baa5c3f87 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-1900000000-54a3d793d6fbf0220b47 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0umi-9200000000-bd780d6ca957af006488 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000f-9800000000-93111d593c96a3298a6c | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-014u-9600000000-5b8e271f29d04a87c89a | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available |
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1D NMR | 1H NMR Spectrum | Not Available |
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1D NMR | 1H NMR Spectrum | Not Available |
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2D NMR | [1H,1H] 2D NMR Spectrum | Not Available |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
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References |
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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 ]
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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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Material Safety Data Sheet (MSDS) |
Download (PDF) |
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Links |
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External Links: |
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