Identification |
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YMDB ID | YMDB00577 |
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Name | tryptophol |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Tryptophol, also known as indole-3-ethanol, 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. In yeast, tryptophol is involved in the metabolic pathway called the tryptophan metabolism pathway. Based on a literature review a significant number of articles have been published on Tryptophol. |
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Structure | |
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Synonyms | - β-(3-Indole)ethanol
- 1H-Indole-3-ethanol
- 1H-indolyl-3-ethanol
- 2-(1H-Indol-3-yl)ethanol
- 2-(3-Indolyl)ethanol
- 2-(3-Indolylethanol
- 2-(indol-3-yl)ethanol
- 3-(β-Hydroxyethyl)indole
- 3-(2-Hydroxyethyl)indole
- 3-(b-Hydroxyethyl)indole
- 3-(beta-Hydroxyethyl)indole
- 3-Indoleethanol
- 3-Indolylethanol
- b-(3-Indole)ethanol
- beta-(3-Indole)ethanol
- beta-Indol-3-ylethanol
- dl-Tryptophanol
- Ethanol, 2-indol-3-yl-
- Ethanol, 3-indolyl-
- IEA
- Indole ethanol
- Indole-3-ethanol
- Indoleethanol
- Tryptophol
- Tryptophanol
- 3-(2-Hydroxyethyl)-1H-indole
- 3-(β-Hydroxyethyl)indole
- 3-Indole ethanol
- β-(3-Indole)ethanol
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CAS number | 526-55-6 |
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Weight | Average: 161.2004 Monoisotopic: 161.084063979 |
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InChI Key | MBBOMCVGYCRMEA-UHFFFAOYSA-N |
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InChI | 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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IUPAC Name | 2-(1H-indol-3-yl)ethan-1-ol |
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Traditional IUPAC Name | tryptophol |
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Chemical Formula | C10H11NO |
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SMILES | OCCC1=CNC2=CC=CC=C12 |
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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 | Solid |
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Charge | 0 |
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Melting point | 59 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | - extracellular
- mitochondrion
- cytoplasm
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways | |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0udi-1591000000-5b173cc0ac0dc2b874a9 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0udi-1591000000-5b173cc0ac0dc2b874a9 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0udi-0490000000-15708d306e1f75b1e76f | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-0900000000-d2769447ff27a79be367 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00yi-5690000000-765b6a566d2067c199b0 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-03di-0900000000-593c6fbb6f64e16e7f05 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-03e9-0900000000-54f7b6548b8a00c91c3f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-003u-0900000000-fb2793cd76eefaaf45c5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-016r-0900000000-a97ae0f4c1633b83c415 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-014i-0900000000-d00c24bc728f46156c60 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-0900000000-593c6fbb6f64e16e7f05 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03e9-0900000000-54f7b6548b8a00c91c3f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-003u-0900000000-fb2793cd76eefaaf45c5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-016r-0900000000-78c3b34c10c43b6a9317 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-d00c24bc728f46156c60 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-03di-0900000000-d41cd8e81a55b3e00538 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-03di-0900000000-aeba8d28d8681fb1473d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-b46601ffc736985fcdf8 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-014i-2900000000-3e7e36fd8027ab6c9e96 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-003u-0900000000-2ba4c5a87b74cfd62e02 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-01ox-0900000000-5fb5f5b5efe809cbe9ad | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00kf-0900000000-44158c348db109504af4 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014l-6900000000-48b709f034a27e74e73f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0900000000-5927d4ac720f209af38d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-00kf-5900000000-4bc97e2ed06c230bbbde | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0900000000-4807fdc919bf8c468f72 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0900000000-63222dc5b6f22cd7cc13 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-00kf-9800000000-314e270d78e7a9ec16a9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0900000000-3f8e0d1410267c0ad66e | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-bfeeeabc14ffd14b537e | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-001i-2900000000-20fec68981d54c2e7002 | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Vuralhan, Z., Morais, M. A., Tai, S. L., Piper, M. D., Pronk, J. T. (2003). "Identification and characterization of phenylpyruvate decarboxylase genes in Saccharomyces cerevisiae." Appl Environ Microbiol 69:4534-4541.12902239
- Leskovac, V., Trivic, S., Pericin, D. (2002). "The three zinc-containing alcohol dehydrogenases from baker's yeast, Saccharomyces cerevisiae." FEMS Yeast Res 2:481-494.12702265
- Dickinson, J. R., Salgado, L. E., Hewlins, M. J. (2003). "The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae." J Biol Chem 278:8028-8034.12499363
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Synthesis Reference: | Snyder, H. R.; Pilgrim, Frederick J. Preparation of 3-indoleacetic acid; new synthesis of tryptophol. Journal of the American Chemical Society (1948), 70 3770-1. |
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