Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-02-21 08:10:09 UTC |
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Update Date | 2023-02-21 17:15:50 UTC |
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HMDB ID | HMDB0001855 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 5-Hydroxytryptophol |
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Description | 5-Hydroxytryptophol is a relatively minor metabolite of serotonin that is excreted primarily as the glucuronide conjugate in human urine. 5-Hydroxytryptophol becomes more important quantitatively during alcohol intoxication, when a shift in the metabolism of serotonin occurs from 5-hydroxyindole acetic acid toward increased (15-fold higher) formation of 5-hydroxytryptophol due to the inhibition of aldehyde dehydrogenase by ethanol-derived acetaldehyde. Urinary excretion of 5-hydroxytryptophol has also been shown to be markedly increased for several hours following intake of foods rich in serotonin, such as bananas. Wide interspecies variation has been reported in the metabolism serotonin to 5-hydroxytryptophol; 5-Hydroxytryptophol makes up 35% of the excreted serotonin metabolites in the rat on average and 10 to 20% in several other species. Human UDP-glucuronosyltransferase 1A6 (UGT1A6) plays a predominant role in the glucuronidation of 5-hydroxytryptophol by human liver microsomes. (PMID 15258112 ). |
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Structure | InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2 |
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Synonyms | Value | Source |
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5-HTOL | HMDB | 5-Hydroxy-1H-indole-3-ethanol | HMDB | 5-Hydroxy-1H-indole-3-ethanol(9ci) | HMDB | 5-Hydroxy-3-indole | HMDB | 5-Hydroxy-3-indoleacetic acid | HMDB | 5-Hydroxy-indole-acetic acid | HMDB | 5-Hydroxyindoacetic acid | HMDB | 5-Hydroxyindol | HMDB | 5-Hydroxyindolacetate | HMDB | 5-Hydroxyindolacetic acid | HMDB | 5-Hydroxyindole-3-ethanol | HMDB | 5-Hydroxyindole-acetic acid | HMDB | Hydroxyindoleacetic acid | HMDB | Hydroxytryptophol | HMDB, MeSH |
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Chemical Formula | C10H11NO2 |
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Average Molecular Weight | 177.1998 |
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Monoisotopic Molecular Weight | 177.078978601 |
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IUPAC Name | 3-(2-hydroxyethyl)-1H-indol-5-ol |
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Traditional Name | hydroxytryptophol |
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CAS Registry Number | 154-02-9 |
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SMILES | OCCC1=CNC2=CC=C(O)C=C12 |
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InChI Identifier | InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2 |
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InChI Key | KQROHCSYOGBQGJ-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 | - 3-alkylindole
- Hydroxyindole
- Indole
- 1-hydroxy-2-unsubstituted benzenoid
- Substituted pyrrole
- Benzenoid
- Heteroaromatic compound
- Pyrrole
- Azacycle
- Organic oxygen compound
- Alcohol
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organopnictogen 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 | 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 | Experimental Collision Cross Sections |
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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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5-Hydroxytryptophol,1TMS,isomer #1 | C[Si](C)(C)OCCC1=C[NH]C2=CC=C(O)C=C12 | 2096.0 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=C2[NH]C=C(CCO)C2=C1 | 2026.3 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,1TMS,isomer #3 | C[Si](C)(C)N1C=C(CCO)C2=CC(O)=CC=C21 | 2087.7 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TMS,isomer #1 | C[Si](C)(C)OCCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12 | 2063.7 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TMS,isomer #2 | C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12 | 2112.9 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TMS,isomer #3 | C[Si](C)(C)OC1=CC=C2C(=C1)C(CCO)=CN2[Si](C)(C)C | 2070.4 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,3TMS,isomer #1 | C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12 | 2099.5 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,3TMS,isomer #1 | C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12 | 2173.8 | Standard non polar | 33892256 | 5-Hydroxytryptophol,3TMS,isomer #1 | C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12 | 2147.5 | Standard polar | 33892256 | 5-Hydroxytryptophol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=C[NH]C2=CC=C(O)C=C12 | 2366.6 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(CCO)C2=C1 | 2313.5 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C=C(CCO)C2=CC(O)=CC=C21 | 2354.7 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12 | 2585.6 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12 | 2599.2 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCO)=CN2[Si](C)(C)C(C)(C)C | 2583.4 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12 | 2801.7 | Semi standard non polar | 33892256 | 5-Hydroxytryptophol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12 | 2796.0 | Standard non polar | 33892256 | 5-Hydroxytryptophol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12 | 2478.9 | Standard polar | 33892256 |
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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 - 5-Hydroxytryptophol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-0900000000-9d105acbf4bc808f485d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-Hydroxytryptophol GC-MS (2 TMS) - 70eV, Positive | splash10-05fs-4094000000-d1307c11143d51fcfef0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 5-Hydroxytryptophol 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 - 5-Hydroxytryptophol Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-01t9-0900000000-438566644fd2e8ec412e | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 5-Hydroxytryptophol Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-03di-0900000000-8baec8b2c7b82d489fc8 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 5-Hydroxytryptophol Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-07vi-0900000000-c7bb9d840b92b2e189ef | 2012-07-24 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 10V, Positive-QTOF | splash10-03fr-0900000000-db5db754e226df916966 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 20V, Positive-QTOF | splash10-03di-0900000000-dd31d267f7f54ef4d1c6 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 40V, Positive-QTOF | splash10-02ai-1900000000-784614cb940ba83ab52e | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 10V, Negative-QTOF | splash10-004i-0900000000-2e8fd5660c103ab7f3cb | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 20V, Negative-QTOF | splash10-002b-0900000000-2ce11ad613dbaf000b6a | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 40V, Negative-QTOF | splash10-001i-2900000000-39a645eb4fa1a2571f5c | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 10V, Negative-QTOF | splash10-004i-0900000000-ef6ae59e91e658cf298a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 20V, Negative-QTOF | splash10-0005-0900000000-079cf44c5cb8c0abc83a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 40V, Negative-QTOF | splash10-014l-0900000000-988823631fda3bc6aced | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 10V, Positive-QTOF | splash10-01t9-0900000000-c77361097a5dfc6286b3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 20V, Positive-QTOF | splash10-01r2-0900000000-ed0c8a92fe9e18ba8ebc | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 5-Hydroxytryptophol 40V, Positive-QTOF | splash10-001i-2900000000-f8bdbcda86acdd866a00 | 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, CD3OD, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, 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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