Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-02-21 17:14:51 UTC |
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HMDB ID | HMDB0000466 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3-Methylindole |
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Description | 3-Methylindole, or skatole, belongs to the indole family and has a methyl substituent in position 3 of the indole ring. It occurs naturally in feces, beets, and coal tar, and has a strong fecal odor. Its name is derived from skato, the Greek word for dung. It exists as a white crystalline or fine powder solid, and it browns upon aging. 3-Methylindole is produced from tryptophan in the mammalian digestive tract where tryptophan is converted to indoleacetic acid, which decarboxylates to give the methylindole. These reactions are largely driven by the microbiota in the digestive tract. 3-Methylindole is soluble in alcohol and benzene and it gives violet color in potassium ferrocyanide (K4Fe(CN)6.3H2O) mixed with sulfuric acid (H2SO4). Skatole has a double ring system which displays aromaticity that comes from the lone pair electrons on the nitrogen. It is continuous (all atoms in the ring are sp2 hybridized), planar, and follows the 4n+2 rule because it has 10 pi electrons. In a 1994 report released by five top cigarette companies, skatole was listed as one of the 599 additives to cigarettes. This is because in low concentrations skatole has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana. As a result, skatole/3-methylindole is used as a fragrance and fixative in many perfumes and as a general aroma compound for other applications. 3-Methylindole has been found to be a bacterial metabolite of members of the Clostridium (PMID: 18223109 ) and Lactobacillus (PMID: 16345702 ) families. Skatole functions as an insect attractant and is one of many compounds that are attractive to males of various species of orchid bees, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait for these bees for study (PMID: 12647866 ). It is also known for being an attractant for the Tasmanian grass grub beetle (Aphodius tasmaniae). Skatole has also been shown to be an attractant to gravid mosquitoes in both field and laboratory conditions (PMID: 24242053 ). |
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Structure | InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3 |
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Synonyms | Value | Source |
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3-Methyl-4,5-benzopyrrole | ChEBI | beta-Methylindole | ChEBI | Skatol | ChEBI | b-Methylindole | Generator | Β-methylindole | Generator | 3-Methyl-1H-indole | HMDB | 3-MI | HMDB | Scatole | HMDB | Skatole | HMDB | 3 Methylindole | HMDB | 3-Methylindole | ChEBI |
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Chemical Formula | C9H9N |
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Average Molecular Weight | 131.1745 |
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Monoisotopic Molecular Weight | 131.073499293 |
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IUPAC Name | 3-methyl-1H-indole |
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Traditional Name | scatole |
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CAS Registry Number | 83-34-1 |
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SMILES | CC1=CNC2=CC=CC=C12 |
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InChI Identifier | InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3 |
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InChI Key | ZFRKQXVRDFCRJG-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 3-methylindoles. These are aromatic heterocyclic compounds that contain an indole moiety substituted at the 3-position with a methyl group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Indoles |
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Direct Parent | 3-methylindoles |
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Alternative Parents | |
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Substituents | - 3-methylindole
- Benzenoid
- Substituted pyrrole
- Heteroaromatic compound
- Pyrrole
- Azacycle
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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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 | 97.5 °C | Not Available | Boiling Point | 265.00 to 266.00 °C. @ 755.00 mm Hg | The Good Scents Company Information System | Water Solubility | 0.5 mg/mL | Not Available | LogP | 2.60 | HANSCH,C ET AL. (1995) |
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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-Methylindole,1TMS,isomer #1 | CC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 1599.7 | Semi standard non polar | 33892256 | 3-Methylindole,1TMS,isomer #1 | CC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 1508.5 | Standard non polar | 33892256 | 3-Methylindole,1TMS,isomer #1 | CC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 1695.4 | Standard polar | 33892256 | 3-Methylindole,1TBDMS,isomer #1 | CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 1831.2 | Semi standard non polar | 33892256 | 3-Methylindole,1TBDMS,isomer #1 | CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 1700.0 | Standard non polar | 33892256 | 3-Methylindole,1TBDMS,isomer #1 | CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 1843.4 | Standard 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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Experimental GC-MS | GC-MS Spectrum - 3-Methylindole EI-B (Non-derivatized) | splash10-0ufr-9200000000-251c9585af60abc11fb1 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3-Methylindole EI-B (Non-derivatized) | splash10-0ufr-9200000000-251c9585af60abc11fb1 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Methylindole GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-1900000000-f9bb0d50c5d49c2c6c4a | 2017-07-27 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Methylindole GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Methylindole GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-001i-2900000000-dba6ed7df0e1ee94cafe | 2015-03-01 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methylindole Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-001i-0900000000-a7cd474bc90f9a0227e5 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methylindole Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-014i-2900000000-cb7f6d8c4ad7b0a1523b | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methylindole Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-000l-9200000000-e9a200fb7b8fc93ced48 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methylindole EI-B (HITACHI M-80) , Positive-QTOF | splash10-0ufr-9200000000-7120fbb6f78f440ff725 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Methylindole Linear Ion Trap , negative-QTOF | splash10-002b-9800000000-a8de490dffcbc2cb0c24 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 10V, Positive-QTOF | splash10-001i-0900000000-355610a12cde08bb25c8 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 20V, Positive-QTOF | splash10-001i-0900000000-36a1bcb0093fec9dd5c5 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 40V, Positive-QTOF | splash10-0zfr-3900000000-d8aebbf9a6779cddc735 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 10V, Negative-QTOF | splash10-001i-0900000000-ed646ab44a1fcc84725b | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 20V, Negative-QTOF | splash10-001i-0900000000-ed6f0939d3598782a893 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 40V, Negative-QTOF | splash10-0f89-2900000000-a801a40b2fcba369d3d4 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 10V, Negative-QTOF | splash10-001i-0900000000-244a9c7ac26f19950926 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 20V, Negative-QTOF | splash10-001i-0900000000-e7c79bc3a884b9bd7abe | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 40V, Negative-QTOF | splash10-004i-1900000000-e057600f7f225ff9cec2 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 10V, Positive-QTOF | splash10-001i-0900000000-f53b130d6fbd7a49b7bd | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 20V, Positive-QTOF | splash10-001i-0900000000-92ee6b9af4d8ea4f32d4 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylindole 40V, Positive-QTOF | splash10-0v00-7900000000-f01b3fb9a64effb7bb2e | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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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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Feces | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Feces | Detected and Quantified | 12189.869 nmol/g wet feces | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 2248.913 nmol/g wet feces | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 2975.68 nmol/g wet feces | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | autism | | details | Feces | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Pervasive Developmental Disorder Not Otherwise Specified | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Ulcerative colitis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Crohn's disease | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Nonalcoholic fatty liver disease (NAFLD) | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Campylobacter jejuni infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Clostridium difficile infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Ulcerative Colitis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Immunoglobulin A nephropathy (IgAN) non progressor | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Immunoglobulin A nephropathy (IgAN) progressor | | details |
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Associated Disorders and Diseases |
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Disease References | Ulcerative colitis |
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- Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
- De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
| Nonalcoholic fatty liver disease |
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- Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
| Autism |
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- De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
| Pervasive developmental disorder not otherwise specified |
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- De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
| Crohn's disease |
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- De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
| 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 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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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 | FDB004302 |
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KNApSAcK ID | C00001430 |
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Chemspider ID | 6480 |
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KEGG Compound ID | C08313 |
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BioCyc ID | SKATOLE |
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BiGG ID | Not Available |
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Wikipedia Link | Skatole |
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METLIN ID | 5453 |
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PubChem Compound | 6736 |
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PDB ID | Not Available |
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ChEBI ID | 9171 |
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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 | rw1006331 |
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References |
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Synthesis Reference | Xu, Jianguo; Xu, Lili; Shi, Hongxin. Synthesis of 3-methylindole and its new purification method. Huagong Shengchan Yu Jishu (2005), 12(4), 12-14. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Karlin DA, Mastromarino AJ, Jones RD, Stroehlein JR, Lorentz O: Fecal skatole and indole and breath methane and hydrogen in patients with large bowel polyps or cancer. J Cancer Res Clin Oncol. 1985;109(2):135-41. [PubMed:3980562 ]
- Moore JG, Jessop LD, Osborne DN: Gas-chromatographic and mass-spectrometric analysis of the odor of human feces. Gastroenterology. 1987 Dec;93(6):1321-9. [PubMed:3678751 ]
- Cooke M, Leeves N, White C: Time profile of putrescine, cadaverine, indole and skatole in human saliva. Arch Oral Biol. 2003 Apr;48(4):323-7. [PubMed:12663078 ]
- Zuccato E, Venturi M, Di Leo G, Colombo L, Bertolo C, Doldi SB, Mussini E: Role of bile acids and metabolic activity of colonic bacteria in increased risk of colon cancer after cholecystectomy. Dig Dis Sci. 1993 Mar;38(3):514-9. [PubMed:8444084 ]
- Muller T, Thissen R, Braun S, Dott W, Fischer G: (M)VOC and composting facilities. Part 2: (M)VOC dispersal in the environment. Environ Sci Pollut Res Int. 2004;11(3):152-7. [PubMed:15259697 ]
- Codipilly DP, Kaufman HW, Kleinberg I: Use of a novel group of oral malodor measurements to evaluate an anti-oral malodor mouthrinse (TriOralTM) in humans. J Clin Dent. 2004;15(4):98-104. [PubMed:15794454 ]
- Whitehead TR, Price NP, Drake HL, Cotta MA: Catabolic pathway for the production of skatole and indoleacetic acid by the acetogen Clostridium drakei, Clostridium scatologenes, and swine manure. Appl Environ Microbiol. 2008 Mar;74(6):1950-3. doi: 10.1128/AEM.02458-07. Epub 2008 Jan 25. [PubMed:18223109 ]
- Yokoyama MT, Carlson JR: Production of Skatole and para-Cresol by a Rumen Lactobacillus sp. Appl Environ Microbiol. 1981 Jan;41(1):71-6. [PubMed:16345702 ]
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