Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2024-04-19 09:27:36 UTC |
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NP-MRD ID | NP0000192 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Indoxyl sulfate |
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Description | Indoxyl sulfate is a dietary protein metabolite and also a metabolite of the common amino acid tryptophan. Indoxyl sulfate is a circulating uremic toxin stimulating glomerular sclerosis and interstitial fibrosis. Indoxyl sulfate is one of the well-known substances of a group of protein-bound uremic retention solutes. Indoxyl sulfate increases the rate of progression of renal failure. In plasma, indoxyl sulfate is a protein-bound uremic solute that induces endothelial dysfunction by inhibiting endothelial proliferation and migration in vitro. Some studies suggest that indoxyl sulfate is also involved in oxidative stress. In hemodialyzed patients, serum levels of indoxyl sulfate are associated with levels of pentosidine, a marker of carbonyl and oxidative stress. In vitro, indoxyl sulfate increases reactive oxygen species (ROS) production in tubular cells and increases NAD(P)H oxidase activity in endothelial cells. Indoxyl sulfate impairs osteoblast function and induces abnormalities of bone turnover. Indoxyl sulfate strongly decreases the levels of glutathione, one of the most active antioxidant systems of the cell (PMID: 10681668 , 14681860 , 17471003 , 17403109 ). |
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Structure | OS(=O)(=O)OC1=CNC2=CC=CC=C12 InChI=1S/C8H7NO4S/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8/h1-5,9H,(H,10,11,12) |
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Synonyms | Value | Source |
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3-Indolyl hydrogen sulfate | ChEBI | 3-Indolyl sulfate | ChEBI | 3-Indoxyl sulfate | ChEBI | 3-Indoxylsulfuric acid | ChEBI | Indican | ChEBI | indol-3-yl Hydrogen sulfate | ChEBI | indol-3-yl Sulfate | ChEBI | indol-3-yl Sulphate | ChEBI | Indoxyl sulfic acid | ChEBI | Indoxyl sulphate | ChEBI | Indoxyl-3-sulphate | ChEBI | Indoxylsulfuric acid | ChEBI | 3-Indolyl hydrogen sulfuric acid | Generator | 3-Indolyl hydrogen sulphate | Generator | 3-Indolyl hydrogen sulphuric acid | Generator | 3-Indolyl sulfuric acid | Generator | 3-Indolyl sulphate | Generator | 3-Indolyl sulphuric acid | Generator | 3-Indoxyl sulfuric acid | Generator | 3-Indoxyl sulphate | Generator | 3-Indoxyl sulphuric acid | Generator | 3-Indoxylsulfate | Generator | 3-Indoxylsulphate | Generator | 3-Indoxylsulphuric acid | Generator | indol-3-yl Hydrogen sulfuric acid | Generator | indol-3-yl Hydrogen sulphate | Generator | indol-3-yl Hydrogen sulphuric acid | Generator | indol-3-yl Sulfuric acid | Generator | indol-3-yl Sulphuric acid | Generator | Indoxyl sulfuric acid | Generator | Indoxyl sulphuric acid | Generator | Indoxyl-3-sulfate | Generator | Indoxyl-3-sulfuric acid | Generator | Indoxyl-3-sulphuric acid | Generator | Indoxylsulfate | Generator | Indoxylsulphate | Generator | Indoxylsulphuric acid | Generator | 1H-indol-3-yl Hydrogen sulfate | HMDB | 1H-indol-3-yl Hydrogen sulphate | HMDB | indol-3-Ol | HMDB | Indican monosodium salt | HMDB | Monopotassium salt, indican | HMDB | Monosodium salt, indican | HMDB | Sulfate, indoxyl | HMDB | Indican monopotassium salt | HMDB | 1H-indol-3-Ol hydrogen sulfate ester | HMDB | 3-Sulphooxy-1H-indole | HMDB | Indoxyl sulfate | Generator |
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Chemical Formula | C8H7NO4S |
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Average Mass | 213.2100 Da |
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Monoisotopic Mass | 213.00958 Da |
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IUPAC Name | (1H-indol-3-yl)oxidanesulfonic acid |
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Traditional Name | 3-sulfooxy-1H-indole |
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CAS Registry Number | 487-94-5 |
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SMILES | OS(=O)(=O)OC1=CNC2=CC=CC=C12 |
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InChI Identifier | InChI=1S/C8H7NO4S/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8/h1-5,9H,(H,10,11,12) |
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InChI Key | BXFFHSIDQOFMLE-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether 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 | Arylsulfates |
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Alternative Parents | |
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Substituents | - Arylsulfate
- Indole
- Indole or derivatives
- Substituted pyrrole
- Sulfuric acid monoester
- Sulfate-ester
- Sulfuric acid ester
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Organoheterocyclic compound
- Azacycle
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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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General References | - Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. [PubMed:8257730 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed:6321058 ]
- Aoyama I, Miyazaki T, Niwa T: Preventive effects of an oral sorbent on nephropathy in rats. Miner Electrolyte Metab. 1999 Jul-Dec;25(4-6):365-72. [PubMed:10681668 ]
- Brunet P, Dou L, Cerini C, Berland Y: Protein-bound uremic retention solutes. Adv Ren Replace Ther. 2003 Oct;10(4):310-20. [PubMed:14681860 ]
- Iwasaki Y: [Uremic toxins and bone metabolism]. Clin Calcium. 2007 May;17(5):734-9. [PubMed:17471003 ]
- Dou L, Jourde-Chiche N, Faure V, Cerini C, Berland Y, Dignat-George F, Brunet P: The uremic solute indoxyl sulfate induces oxidative stress in endothelial cells. J Thromb Haemost. 2007 Jun;5(6):1302-8. [PubMed:17403109 ]
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