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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2013-03-15 15:57:54 UTC |
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Update Date | 2020-11-09 23:21:29 UTC |
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HMDB ID | HMDB0059911 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Paracetamol sulfate |
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Description | Paracetamol sulfate, also known as paracetamol sulfuric acid or 4-acetaminophen sulfate, is classified as a phenylsulfate. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. Paracetamol sulfate is considered a slightly soluble (in water), acidic compound. Paracetamol sulfate is a metabolite of paracetamol, a common drug used for the relief of pain as an antipyretic. After paracetamol is absorbed from the gastrointestinal tract, it forms paracetamol sulfate by conjugation with sulfuric acid. Paracetamol sulfate can be found in both plasma and urine (PMID: 15127815 ). |
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Structure | |
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Synonyms | Value | Source |
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4-Acetaminophen sulfate | ChEBI | Acetaminophen sulfate | ChEBI | Acetaminophen sulfate ester | ChEBI | N-(4-(Sulfooxy)phenyl)acetamide | ChEBI | N-Acetyl-4-aminophenol sulfate | ChEBI | 4-Acetaminophen sulfuric acid | Generator | 4-Acetaminophen sulphate | Generator | 4-Acetaminophen sulphuric acid | Generator | Acetaminophen sulfuric acid | Generator | Acetaminophen sulphate | Generator | Acetaminophen sulphuric acid | Generator | Acetaminophen sulfuric acid ester | Generator | Acetaminophen sulphate ester | Generator | Acetaminophen sulphuric acid ester | Generator | N-(4-(Sulphooxy)phenyl)acetamide | Generator | N-Acetyl-4-aminophenol sulfuric acid | Generator | N-Acetyl-4-aminophenol sulphate | Generator | N-Acetyl-4-aminophenol sulphuric acid | Generator | Paracetamol sulfuric acid | Generator | Paracetamol sulphate | Generator | Paracetamol sulphuric acid | Generator | Acetaminophen sulfate ester, monopotassium salt | HMDB | Acetaminophen-sulfate | HMDB |
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Chemical Formula | C8H9NO5S |
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Average Molecular Weight | 231.226 |
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Monoisotopic Molecular Weight | 231.020143093 |
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IUPAC Name | (4-acetamidophenyl)oxidanesulfonic acid |
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Traditional Name | acetaminophen sulfate |
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CAS Registry Number | 10066-90-7 |
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SMILES | CC(=O)NC1=CC=C(OS(O)(=O)=O)C=C1 |
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InChI Identifier | InChI=1S/C8H9NO5S/c1-6(10)9-7-2-4-8(5-3-7)14-15(11,12)13/h2-5H,1H3,(H,9,10)(H,11,12,13) |
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InChI Key | IGTYILLPRJOVFY-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic sulfuric acids and derivatives |
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Sub Class | Arylsulfates |
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Direct Parent | Phenylsulfates |
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Alternative Parents | |
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Substituents | - Phenylsulfate
- Phenoxy compound
- Monocyclic benzene moiety
- Sulfuric acid monoester
- Benzenoid
- Sulfuric acid ester
- Sulfate-ester
- Carboximidic acid
- Carboximidic acid derivative
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- 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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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: |
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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-052u-1910000000-4ee58d86bf185f461627 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0190000000-5bad922abf676bb4b1f0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f89-1940000000-7efc6683f5827c5c7a28 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0hb9-4920000000-f9c40a12b34dc5c8873f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0290000000-32990649c8c1c547530d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zgr-0920000000-ed846e515158c2272d36 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a59-2900000000-b2669c115f7c413a29b1 | 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 | |
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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 | Normal | | 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 and Quantified | 138.6 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
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Associated OMIM IDs | |
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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 | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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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 | 83939 |
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PDB ID | Not Available |
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ChEBI ID | 32635 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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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 | - Jensen LS, Valentine J, Milne RW, Evans AM: The quantification of paracetamol, paracetamol glucuronide and paracetamol sulphate in plasma and urine using a single high-performance liquid chromatography assay. J Pharm Biomed Anal. 2004 Feb 18;34(3):585-93. [PubMed:15127815 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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