Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-04-12 16:30:20 UTC |
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Update Date | 2021-09-14 15:20:06 UTC |
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HMDB ID | HMDB0005874 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3-Bromotyrosine |
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Description | 3-Bromotyrosine(BY) is generated from the halogenation of tyrosine residues in plasma proteins via the enzyme Eosinophil peroxidase. The presence of free bromotyrosine in blood or urine is the result of enzymatic degradation of these brominated proteins. A significantly higher concentration of BY was observed in the urine from asthmatic patients than in that from healthy control subjects (PMID: 15196282 ). Bromotyrosine may be useful for monitoring the activation of eosinophils in asthmatic patients. |
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Structure | NC(CC1=CC=C(O)C(Br)=C1)C(O)=O InChI=1S/C9H10BrNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14) |
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Synonyms | Value | Source |
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3-Bromo-DL-tyrosine | MeSH | 3-Bromo-tyr | MeSH | 3-bromo-Tyrosine | HMDB | Bromotyrosine | HMDB | 3-Bromotyrosine | KEGG |
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Chemical Formula | C9H10BrNO3 |
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Average Molecular Weight | 260.085 |
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Monoisotopic Molecular Weight | 258.984405838 |
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IUPAC Name | 2-amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid |
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Traditional Name | 2-amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid |
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CAS Registry Number | 54788-30-6 |
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SMILES | NC(CC1=CC=C(O)C(Br)=C1)C(O)=O |
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InChI Identifier | InChI=1S/C9H10BrNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14) |
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InChI Key | HGWOSUKIFQMEIF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Tyrosine and derivatives |
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Alternative Parents | |
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Substituents | - Tyrosine or derivatives
- Phenylalanine or derivatives
- 3-phenylpropanoic-acid
- Alpha-amino acid
- Amphetamine or derivatives
- 2-bromophenol
- 2-halophenol
- 1-hydroxy-2-unsubstituted benzenoid
- Halobenzene
- Phenol
- Bromobenzene
- Aralkylamine
- Aryl halide
- Aryl bromide
- Benzenoid
- Monocyclic benzene moiety
- Amino acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic nitrogen compound
- Organohalogen compound
- Primary aliphatic amine
- Organobromide
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- Primary amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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3-Bromotyrosine,1TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(CC(N)C(=O)O)C=C1Br | 2134.5 | Semi standard non polar | 33892256 | 3-Bromotyrosine,1TMS,isomer #2 | C[Si](C)(C)OC(=O)C(N)CC1=CC=C(O)C(Br)=C1 | 2057.4 | Semi standard non polar | 33892256 | 3-Bromotyrosine,1TMS,isomer #3 | C[Si](C)(C)NC(CC1=CC=C(O)C(Br)=C1)C(=O)O | 2155.9 | Semi standard non polar | 33892256 | 3-Bromotyrosine,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(N)CC1=CC=C(O[Si](C)(C)C)C(Br)=C1 | 2089.5 | Semi standard non polar | 33892256 | 3-Bromotyrosine,2TMS,isomer #2 | C[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C)C(Br)=C1)C(=O)O | 2141.2 | Semi standard non polar | 33892256 | 3-Bromotyrosine,2TMS,isomer #3 | C[Si](C)(C)NC(CC1=CC=C(O)C(Br)=C1)C(=O)O[Si](C)(C)C | 2071.1 | Semi standard non polar | 33892256 | 3-Bromotyrosine,2TMS,isomer #4 | C[Si](C)(C)N(C(CC1=CC=C(O)C(Br)=C1)C(=O)O)[Si](C)(C)C | 2276.0 | Semi standard non polar | 33892256 | 3-Bromotyrosine,3TMS,isomer #1 | C[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C)C(Br)=C1)C(=O)O[Si](C)(C)C | 2104.3 | Semi standard non polar | 33892256 | 3-Bromotyrosine,3TMS,isomer #1 | C[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C)C(Br)=C1)C(=O)O[Si](C)(C)C | 2131.4 | Standard non polar | 33892256 | 3-Bromotyrosine,3TMS,isomer #1 | C[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C)C(Br)=C1)C(=O)O[Si](C)(C)C | 2272.6 | Standard polar | 33892256 | 3-Bromotyrosine,3TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1Br | 2306.5 | Semi standard non polar | 33892256 | 3-Bromotyrosine,3TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1Br | 2199.8 | Standard non polar | 33892256 | 3-Bromotyrosine,3TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1Br | 2447.6 | Standard polar | 33892256 | 3-Bromotyrosine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Br)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2217.2 | Semi standard non polar | 33892256 | 3-Bromotyrosine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Br)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2169.3 | Standard non polar | 33892256 | 3-Bromotyrosine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Br)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2425.5 | Standard polar | 33892256 | 3-Bromotyrosine,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(Br)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2323.1 | Semi standard non polar | 33892256 | 3-Bromotyrosine,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(Br)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2252.4 | Standard non polar | 33892256 | 3-Bromotyrosine,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(Br)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2225.5 | Standard polar | 33892256 | 3-Bromotyrosine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(CC(N)C(=O)O)C=C1Br | 2391.7 | Semi standard non polar | 33892256 | 3-Bromotyrosine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC=C(O)C(Br)=C1 | 2330.7 | Semi standard non polar | 33892256 | 3-Bromotyrosine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O)C(Br)=C1)C(=O)O | 2418.2 | Semi standard non polar | 33892256 | 3-Bromotyrosine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Br)=C1 | 2635.2 | Semi standard non polar | 33892256 | 3-Bromotyrosine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Br)=C1)C(=O)O | 2678.2 | Semi standard non polar | 33892256 | 3-Bromotyrosine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O)C(Br)=C1)C(=O)O[Si](C)(C)C(C)(C)C | 2561.3 | Semi standard non polar | 33892256 | 3-Bromotyrosine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(C(CC1=CC=C(O)C(Br)=C1)C(=O)O)[Si](C)(C)C(C)(C)C | 2711.9 | Semi standard non polar | 33892256 | 3-Bromotyrosine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Br)=C1)C(=O)O[Si](C)(C)C(C)(C)C | 2863.1 | Semi standard non polar | 33892256 | 3-Bromotyrosine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Br)=C1)C(=O)O[Si](C)(C)C(C)(C)C | 2710.0 | Standard non polar | 33892256 | 3-Bromotyrosine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Br)=C1)C(=O)O[Si](C)(C)C(C)(C)C | 2649.5 | Standard polar | 33892256 | 3-Bromotyrosine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1Br | 3015.2 | Semi standard non polar | 33892256 | 3-Bromotyrosine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1Br | 2750.0 | Standard non polar | 33892256 | 3-Bromotyrosine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1Br | 2728.6 | Standard polar | 33892256 | 3-Bromotyrosine,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Br)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2886.7 | Semi standard non polar | 33892256 | 3-Bromotyrosine,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Br)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2780.6 | Standard non polar | 33892256 | 3-Bromotyrosine,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(Br)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2696.0 | Standard polar | 33892256 | 3-Bromotyrosine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Br)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3222.9 | Semi standard non polar | 33892256 | 3-Bromotyrosine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Br)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2933.3 | Standard non polar | 33892256 | 3-Bromotyrosine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(Br)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2656.3 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 3-Bromotyrosine GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-7950000000-90477459776ef78e016c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Bromotyrosine GC-MS (2 TMS) - 70eV, Positive | splash10-000i-7192000000-4db2f995c979f5e8dc5b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Bromotyrosine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 10V, Positive-QTOF | splash10-08fu-0190000000-09f7228b1b38718c469e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 20V, Positive-QTOF | splash10-03di-0690000000-b5820783ee8b9a4da08d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 40V, Positive-QTOF | splash10-0kai-1900000000-a37bf7cc9fad6990a82c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 10V, Negative-QTOF | splash10-0a4i-0090000000-8979862cf5482b3b717e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 20V, Negative-QTOF | splash10-0a4r-1290000000-36c22d910365b774ed54 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 40V, Negative-QTOF | splash10-00di-9620000000-1240e96d89e8523fefc4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 10V, Positive-QTOF | splash10-03di-0090000000-c65d0fe7e926dbe614b1 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 20V, Positive-QTOF | splash10-03di-0490000000-b15e78d4e91b2476869e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 40V, Positive-QTOF | splash10-001i-2900000000-cc7c728c71ac1f2d511b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 10V, Negative-QTOF | splash10-0a4i-2090000000-0e7a223ad655d7ccb757 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 20V, Negative-QTOF | splash10-00ba-9720000000-af58a14ec5398ec9b211 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Bromotyrosine 40V, Negative-QTOF | splash10-00b9-9100000000-042c6fafc59f7fbd82b4 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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