Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-13 10:46:17 UTC |
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Update Date | 2023-02-21 17:16:54 UTC |
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HMDB ID | HMDB0004094 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Indoxyl |
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Description | Indoxyl, also known as 1H-indol-3-ol, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. Indoxyl is isomeric with oxindol and is obtained as an oily liquid. Indoxyl exists in all living organisms, ranging from bacteria to humans. Indoxyl is obtained from indican, which is a glycoside. Obermayer's reagent is a dilute solution FeCl3 in hydrochloric acid. The hydrolysis of indican yields β-D-glucose and indoxyl. Indigo dye is a product of the reaction of indoxyl by a mild oxidizing agent such as atmospheric oxygen. In chemistry, indoxyl is a nitrogenous substance with the chemical formula: C8H7NO. Indoxyl can be found in urine and is titrated with Obermayer's reagent. |
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Structure | InChI=1S/C8H7NO/c10-8-5-9-7-4-2-1-3-6(7)8/h1-5,9-10H |
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Synonyms | Value | Source |
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1H-indol-3-Ol | ChEBI |
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Chemical Formula | C8H7NO |
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Average Molecular Weight | 133.1473 |
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Monoisotopic Molecular Weight | 133.052763851 |
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IUPAC Name | 1H-indol-3-ol |
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Traditional Name | indoxyl |
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CAS Registry Number | 480-93-3 |
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SMILES | OC1=CNC2=CC=CC=C12 |
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InChI Identifier | InChI=1S/C8H7NO/c10-8-5-9-7-4-2-1-3-6(7)8/h1-5,9-10H |
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InChI Key | PCKPVGOLPKLUHR-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl 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 | Hydroxyindoles |
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Direct Parent | Hydroxyindoles |
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Alternative Parents | |
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Substituents | - Hydroxyindole
- Indole
- Benzenoid
- Substituted pyrrole
- Heteroaromatic compound
- Pyrrole
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- 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 | 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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Indoxyl,1TMS,isomer #1 | C[Si](C)(C)OC1=C[NH]C2=CC=CC=C12 | 1602.3 | Semi standard non polar | 33892256 | Indoxyl,1TMS,isomer #2 | C[Si](C)(C)N1C=C(O)C2=CC=CC=C21 | 1706.1 | Semi standard non polar | 33892256 | Indoxyl,2TMS,isomer #1 | C[Si](C)(C)OC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 1782.5 | Semi standard non polar | 33892256 | Indoxyl,2TMS,isomer #1 | C[Si](C)(C)OC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 1708.8 | Standard non polar | 33892256 | Indoxyl,2TMS,isomer #1 | C[Si](C)(C)OC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 1710.5 | Standard polar | 33892256 | Indoxyl,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=C[NH]C2=CC=CC=C12 | 1869.4 | Semi standard non polar | 33892256 | Indoxyl,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C=C(O)C2=CC=CC=C21 | 1958.2 | Semi standard non polar | 33892256 | Indoxyl,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 2156.8 | Semi standard non polar | 33892256 | Indoxyl,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 2120.6 | Standard non polar | 33892256 | Indoxyl,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 2011.6 | Standard polar | 33892256 |
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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 - Indoxyl GC-MS (2 TMS) | splash10-004i-3980000000-520b4525adaeb185fb13 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Indoxyl GC-MS (Non-derivatized) | splash10-004i-3980000000-520b4525adaeb185fb13 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Indoxyl GC-MS (Non-derivatized) - 70eV, Positive | splash10-0kai-1900000000-1c5e163741d871a2c138 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Indoxyl GC-MS (1 TMS) - 70eV, Positive | splash10-0fl3-6910000000-0c8f4cb37b60dcecf8ea | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Indoxyl 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - Indoxyl Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-001i-0900000000-e2d4dbd9b806b29ce214 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indoxyl Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-056r-9500000000-263e6cbbc9fbea4d1fe2 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indoxyl Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-004i-9000000000-601cd8ae4909db7a541a | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indoxyl 10V, Negative-QTOF | splash10-001i-1900000000-0276e7599b0c044e16ca | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indoxyl 20V, Negative-QTOF | splash10-003r-8900000000-1a948ecd165e51423035 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indoxyl 20V, Positive-QTOF | splash10-0a4i-6900000000-e7a7e7fb048f732eb685 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indoxyl 10V, Positive-QTOF | splash10-001i-4900000000-e34a5c59b0cce2170e4f | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indoxyl 40V, Positive-QTOF | splash10-004i-9000000000-271db1608159a875a61c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indoxyl 40V, Negative-QTOF | splash10-0006-9100000000-e357308e88e379d8eb0b | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 10V, Positive-QTOF | splash10-001i-0900000000-ce70e056e1f4cfdf3761 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 20V, Positive-QTOF | splash10-001i-0900000000-9beba85555a54c1f672e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 40V, Positive-QTOF | splash10-0kui-7900000000-c36b8119a51196a1f474 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 10V, Negative-QTOF | splash10-001i-0900000000-0d126f50596b5c4ae9ec | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 20V, Negative-QTOF | splash10-001i-0900000000-d5b63c4616a3ca6983c2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 40V, Negative-QTOF | splash10-0udi-2900000000-f4d199baa93fba2d315c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 10V, Positive-QTOF | splash10-001i-0900000000-ac524f6f858437766e2f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 20V, Positive-QTOF | splash10-001i-1900000000-1064492c92995ca99566 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 40V, Positive-QTOF | splash10-004i-9300000000-62b87115059cfc657adc | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 10V, Negative-QTOF | splash10-001i-0900000000-a956a3a0009c6965897a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 20V, Negative-QTOF | splash10-001i-0900000000-7b07769eadb95204ac58 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indoxyl 40V, Negative-QTOF | splash10-001i-0900000000-fea25d8ed304aa380484 | 2021-09-22 | 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 | Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, 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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