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Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-12 03:37:29 UTC |
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Update Date | 2022-03-07 02:57:09 UTC |
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HMDB ID | HMDB0041706 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Caffeic acid 3-O-sulfate |
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Description | Caffeic acid 3-O-sulfate, also known as caffeate 3'-O-sulphate or caffeic acid 3-sulfuric acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid 3-O-sulfate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Caffeic acid 3-O-sulfate. |
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Structure | OC(=O)\C=C\C1=CC(OS(O)(=O)=O)=C(O)C=C1 InChI=1S/C9H8O7S/c10-7-3-1-6(2-4-9(11)12)5-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+ |
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Synonyms | Value | Source |
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Caffeic acid 3'-O-sulfate | ChEBI | Caffeic acid 3'-sulfate | ChEBI | Caffeic acid 3-sulphate | ChEBI | Caffeate 3'-O-sulfate | Generator | Caffeate 3'-O-sulphate | Generator | Caffeic acid 3'-O-sulfuric acid | Generator | Caffeic acid 3'-O-sulphuric acid | Generator | Caffeate 3'-sulfate | Generator | Caffeate 3'-sulphate | Generator | Caffeic acid 3'-sulfuric acid | Generator | Caffeic acid 3'-sulphuric acid | Generator | Caffeate 3-sulfate | Generator | Caffeate 3-sulphate | Generator | Caffeic acid 3-sulfuric acid | Generator | Caffeic acid 3-sulphuric acid | Generator | Caffeate 3-O-sulfate | Generator | Caffeate 3-O-sulphate | Generator | Caffeic acid 3-O-sulfuric acid | Generator | Caffeic acid 3-O-sulphuric acid | Generator | (2E)-3-[4-Hydroxy-3-(sulfooxy)phenyl]-2-propenoic acid | HMDB | (e)-Caffeic acid 3-O-sulfate | HMDB | (e)-Caffeic acid 3-O-sulphate | HMDB | (e)-Caffeic acid 3-sulfate | HMDB | (e)-Caffeic acid 3-sulphate | HMDB | (e)-Caffeic acid sulfate | HMDB | (e)-Caffeic acid sulphate | HMDB | 3-[4-Hydroxy-3-(sulfooxy)phenyl]-2-propenoic acid | HMDB | Caffeic acid 3-O-sulphate | HMDB | Caffeic acid 3-sulfate | HMDB | Caffeic acid sulfate | HMDB | Caffeic acid sulphate | HMDB | trans-Caffeic acid 3-O-sulfate | HMDB | trans-Caffeic acid 3-O-sulphate | HMDB | trans-Caffeic acid 3-sulfate | HMDB | trans-Caffeic acid 3-sulphate | HMDB | trans-Caffeic acid sulfate | HMDB | trans-Caffeic acid sulphate | HMDB | Caffeic acid 3-O-sulfate | ChEBI |
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Chemical Formula | C9H8O7S |
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Average Molecular Weight | 260.221 |
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Monoisotopic Molecular Weight | 259.9990733 |
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IUPAC Name | (2E)-3-[4-hydroxy-3-(sulfooxy)phenyl]prop-2-enoic acid |
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Traditional Name | (2E)-3-[4-hydroxy-3-(sulfooxy)phenyl]prop-2-enoic acid |
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CAS Registry Number | 151481-52-6 |
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SMILES | OC(=O)\C=C\C1=CC(OS(O)(=O)=O)=C(O)C=C1 |
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InChI Identifier | InChI=1S/C9H8O7S/c10-7-3-1-6(2-4-9(11)12)5-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+ |
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InChI Key | VWQNTRNACRFUCQ-DUXPYHPUSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Cinnamic acids and derivatives |
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Sub Class | Hydroxycinnamic acids and derivatives |
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Direct Parent | Hydroxycinnamic acids |
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Alternative Parents | |
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Substituents | - Cinnamic acid
- Coumaric acid or derivatives
- Hydroxycinnamic acid
- Phenylsulfate
- Arylsulfate
- Phenoxy compound
- Styrene
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Sulfuric acid ester
- Sulfate-ester
- Sulfuric acid monoester
- Organic sulfuric acid or derivatives
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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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 | |
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Physical Properties |
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State | Not Available |
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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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Caffeic acid 3-O-sulfate,1TMS,isomer #1 | C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O)C(OS(=O)(=O)O)=C1 | 2434.2 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O)C=C1OS(=O)(=O)O | 2440.2 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,1TMS,isomer #3 | C[Si](C)(C)OS(=O)(=O)OC1=CC(/C=C/C(=O)O)=CC=C1O | 2470.9 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,2TMS,isomer #1 | C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O)=C1 | 2490.6 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,2TMS,isomer #2 | C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C)=C1 | 2451.3 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,2TMS,isomer #3 | C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O)C=C1OS(=O)(=O)O[Si](C)(C)C | 2490.3 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,3TMS,isomer #1 | C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)=C1 | 2494.4 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,3TMS,isomer #1 | C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)=C1 | 2565.2 | Standard non polar | 33892256 | Caffeic acid 3-O-sulfate,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O)C(OS(=O)(=O)O)=C1 | 2706.0 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O)C=C1OS(=O)(=O)O | 2724.5 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(/C=C/C(=O)O)=CC=C1O | 2735.6 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O)=C1 | 3006.5 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1 | 2969.8 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O)C=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C | 3005.2 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3211.5 | Semi standard non polar | 33892256 | Caffeic acid 3-O-sulfate,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3370.0 | Standard non polar | 33892256 |
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Spectra |
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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 - Caffeic acid 3-O-sulfate GC-MS (Non-derivatized) - 70eV, Positive | splash10-03xu-1690000000-11cf3ed2d92f173f27cc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Caffeic acid 3-O-sulfate GC-MS (2 TMS) - 70eV, Positive | splash10-00dr-5019000000-93ef726d3d90fbb1f5d1 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Caffeic acid 3-O-sulfate 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 - Caffeic acid 3-O-sulfate 10V, Positive-QTOF | splash10-0006-0090000000-1fbaa79aef2070940a38 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 20V, Positive-QTOF | splash10-0j4l-0790000000-8e3aac299e17766efec2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 40V, Positive-QTOF | splash10-0q29-7910000000-91f54071865bef100eeb | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 10V, Negative-QTOF | splash10-0a4i-0090000000-3dfaf420aef92ccf20c3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 20V, Negative-QTOF | splash10-06vi-0950000000-9079a77c64b4f3115a00 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 40V, Negative-QTOF | splash10-03e9-4900000000-942bbc0cc678f5e50dc1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 10V, Negative-QTOF | splash10-067i-0490000000-7d8c68b79b3ef929f350 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 20V, Negative-QTOF | splash10-014j-5290000000-be2fa5928e40e9240e38 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 40V, Negative-QTOF | splash10-05a2-5910000000-15fbdce02e7a7ec55f64 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 10V, Positive-QTOF | splash10-03dl-0980000000-d31a92acfa7ffec23a28 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 20V, Positive-QTOF | splash10-03di-0910000000-a11925c7fa34c6c78a65 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 40V, Positive-QTOF | splash10-014i-0900000000-825e2ebba2493279ecee | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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 | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 941 | | details | Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 941 | | details | Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 941 | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 941 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 941 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 941 | | details |
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Abnormal Concentrations |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB029871 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 30777605 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 102261219 |
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PDB ID | Not Available |
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ChEBI ID | 90242 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]
- Ounnas F, Prive F, Salen P, Gaci N, Tottey W, Calani L, Bresciani L, Lopez-Gutierrez N, Hazane-Puch F, Laporte F, Brugere JF, Del Rio D, Demeilliers C, de Lorgeril M: Whole Rye Consumption Improves Blood and Liver n-3 Fatty Acid Profile and Gut Microbiota Composition in Rats. PLoS One. 2016 Feb 10;11(2):e0148118. doi: 10.1371/journal.pone.0148118. eCollection 2016. [PubMed:26862900 ]
- Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]
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