| Record Information |
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| Version | 2.0 |
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| Created at | 2025-07-14 15:50:35 UTC |
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| Updated at | 2025-09-22 01:00:52 UTC |
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| NP-MRD ID | NP0351316 |
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| Natural Product DOI | https://doi.org/10.57994/4322 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Tryptophol |
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| Description | Tryptophol, also known as 3-indoleethanol or IEA, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Tryptophol exists in all living species, ranging from bacteria to plants to humans. Tryptophol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Tryptophol was first documented in 1981 (PMID: 7241135). Based on a literature review a significant number of articles have been published on Tryptophol (PMID: 27814509) (PMID: 16664264) (PMID: 19842066) (PMID: 10856636) (PMID: 12499363) (PMID: 23413824). |
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| Structure | [H]OC([H])([H])C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2 |
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| Synonyms | | Value | Source |
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| 1H-Indole-3-ethanol | ChEBI | | 1H-Indolyl-3-ethanol | ChEBI | | 2-(indol-3-yl)Ethanol | ChEBI | | 3-(2-Hydroxyethyl)indole | ChEBI | | Indole-3-ethanol | ChEBI | | Tryptophanol | ChEBI | | 2-(1H-indol-3-yl)Ethanol | HMDB | | 2-(3-Indolyl)ethanol | HMDB | | 2-(3-Indolylethanol | HMDB | | 3-(b-Hydroxyethyl)indole | HMDB | | 3-(beta-Hydroxyethyl)indole | HMDB | | 3-Indoleethanol | HMDB | | 3-Indolylethanol | HMDB | | b-(3-Indole)ethanol | HMDB | | beta-(3-Indole)ethanol | HMDB | | beta-indol-3-Ylethanol | HMDB | | DL-Tryptophanol | HMDB | | IEA | HMDB | | Indole ethanol | HMDB | | Indoleethanol | HMDB | | 3-(2-Hydroxyethyl)-1H-indole | HMDB | | 3-(Β-hydroxyethyl)indole | HMDB | | 3-Indole ethanol | HMDB | | Β-(3-indole)ethanol | HMDB | | Tryptophol | HMDB, KEGG |
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| Chemical Formula | C10H11NO |
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| Average Mass | 161.2004 Da |
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| Monoisotopic Mass | 161.08406 Da |
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| IUPAC Name | 2-(1H-indol-3-yl)ethan-1-ol |
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| Traditional Name | tryptophol |
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| CAS Registry Number | Not Available |
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| SMILES | [H]OC([H])([H])C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 |
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| InChI Identifier | InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2 |
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| InChI Key | MBBOMCVGYCRMEA-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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| COSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | sanjeevan.chem@gmail.com | University of North Texas | Sanjeevan Rajendran | 2025-09-21 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | sanjeevan.chem@gmail.com | University of North Texas | Sanjeevan Rajendran | 2025-09-21 | View Spectrum | | HMQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | sanjeevan.chem@gmail.com | University of North Texas | Sanjeevan Rajendran | 2025-09-21 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, CD3OD, experimental) | sanjeevan.chem@gmail.com | University of North Texas | Sanjeevan Rajendran | 2025-09-21 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | sanjeevan.chem@gmail.com | University of North Texas | Sanjeevan Rajendran | 2025-09-21 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | sanjeevan.chem@gmail.com | University of North Texas | Sanjeevan Rajendran | 2025-09-21 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental) | sanjeevan.chem@gmail.com | University of North Texas | Sanjeevan Rajendran | 2025-09-21 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | rjm4kd@umsystem.edu | Sumner lab, University of Missouri | Ronald Myers | 2025-07-14 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | rjm4kd@umsystem.edu | Sumner lab, University of Missouri | Ronald Myers | 2025-07-14 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | rjm4kd@umsystem.edu | Sumner lab, University of Missouri | Ronald Myers | 2025-07-14 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | rjm4kd@umsystem.edu | Sumner lab, University of Missouri | Ronald Myers | 2025-07-14 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600.0 MHz, C2D6OS, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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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, 600.0, C2D6OS, simulated) | rjm4kd@umsystem.edu | Sumner lab, University of Missouri | Ronald Myers | 2025-07-14 | View Spectrum |
| | Species |
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| Species of Origin | | Species Name | Source | Reference |
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| Colletotrichum spinosum | | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. |
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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-alkylindoles |
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| Alternative Parents | |
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| Substituents | - 3-alkylindole
- Benzenoid
- Substituted pyrrole
- Heteroaromatic compound
- Pyrrole
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- 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 | Not Available |
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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 | - Cornford EM, Crane PD, Braun LD, Bocash WD, Nyerges AM, Oldendorf WH: Reduction in brain glucose utilization rate after tryptophol (3-indole ethanol) treatment. J Neurochem. 1981 May;36(5):1758-65. [PubMed:7241135 ]
- Schirmer M, Smeekens SP, Vlamakis H, Jaeger M, Oosting M, Franzosa EA, Ter Horst R, Jansen T, Jacobs L, Bonder MJ, Kurilshikov A, Fu J, Joosten LAB, Zhernakova A, Huttenhower C, Wijmenga C, Netea MG, Xavier RJ: Linking the Human Gut Microbiome to Inflammatory Cytokine Production Capacity. Cell. 2016 Nov 3;167(4):1125-1136.e8. doi: 10.1016/j.cell.2016.10.020. [PubMed:27814509 ]
- Lacan G, Magnus V, Simaga S, Iskric S, Hall PJ: Metabolism of tryptophol in higher and lower plants. Plant Physiol. 1985 Jul;78(3):447-54. doi: 10.1104/pp.78.3.447. [PubMed:16664264 ]
- Elleuch L, Shaaban M, Smaoui S, Mellouli L, Karray-Rebai I, Fourati-Ben Fguira L, Shaaban KA, Laatsch H: Bioactive secondary metabolites from a new terrestrial Streptomyces sp. TN262. Appl Biochem Biotechnol. 2010 Sep;162(2):579-93. doi: 10.1007/s12010-009-8808-4. Epub 2009 Oct 20. [PubMed:19842066 ]
- Erdoğan I I, Sener B, Higa T: Tryptophol, a plant auxin isolated from the marine sponge Ircinia spinulosa. Biochem Syst Ecol. 2000 Oct 1;28(8):793-794. doi: 10.1016/s0305-1978(99)00111-8. [PubMed:10856636 ]
- Dickinson JR, Salgado LE, Hewlins MJ: The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae. J Biol Chem. 2003 Mar 7;278(10):8028-34. doi: 10.1074/jbc.M211914200. Epub 2002 Dec 23. [PubMed:12499363 ]
- Zupan J, Avbelj M, Butinar B, Kosel J, Sergan M, Raspor P: Monitoring of quorum-sensing molecules during minifermentation studies in wine yeast. J Agric Food Chem. 2013 Mar 13;61(10):2496-505. doi: 10.1021/jf3051363. Epub 2013 Mar 5. [PubMed:23413824 ]
- Nazari F, Sulyok M, Yazdanpanah H, Kobarfard F, Krska R: A survey of mycotoxins in domestic rice in Iran by liquid chromatography tandem mass spectrometry. Toxicol Mech Methods. 2014 Jan;24(1):37-41. doi: 10.3109/15376516.2013.844752. Epub 2013 Oct 28. [PubMed:24032669 ]
- Sandberg G: Biosynthesis and metabolism of indole-3-ethanol and indole-3-acetic acid by Pinus sylvestris L. needles. Planta. 1984 Jul;161(5):398-403. doi: 10.1007/BF00394569. [PubMed:24253838 ]
- Eze F, Schoellhorn S, Grinffiel D, Chapman K, Rajendran S, Skellam E: Assessing the Biosynthetic Potential of the Bioherbicide Colletotrichum spinosum CBS 515.97: Discovery of 3"-Demethylthielavin M and Assorted Alkaloids. Chem Biodivers. 2025 Aug 14:e01247. doi: 10.1002/cbdv.202501247. [PubMed:40812239 ]
- DOI: 10.1002/cbdv.202501247
- PMID: 40812239
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