Record Information |
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Version | 1.0 |
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Created at | 2022-02-14 20:40:15 UTC |
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Updated at | 2022-03-10 22:21:21 UTC |
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NP-MRD ID | NP0044262 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Indoleacetaldehyde |
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Description | Indoleacetaldehyde, also known as tryptaldehyde, 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. An indoleacetaldehyde that is acetaldehyde in which one of the methyl hydrogens are replaced by a indol-3-yl group. Indoleacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Indoleacetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, indoleacetaldehyde participates in a number of enzymatic reactions. In particular, indoleacetaldehyde can be biosynthesized from tryptamine; which is mediated by the enzyme kynurenine 3-monooxygenase. In addition, indoleacetaldehyde can be converted into indoleacetic acid through its interaction with the enzyme aldehyde dehydrogenase, mitochondrial. In humans, indoleacetaldehyde is involved in tryptophan metabolism. Outside of the human body, Indoleacetaldehyde has been detected, but not quantified in, several different foods, such as ohelo berries, mamey sapotes, turnips, chives, and pummelo. This could make indoleacetaldehyde a potential biomarker for the consumption of these foods. Indoleacetaldehyde is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
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Structure | InChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2 |
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Synonyms | Value | Source |
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1H-Indole-3-acetaldehyde | ChEBI | 2-(indol-3-yl)Acetaldehyde | ChEBI | Indole-3-acetaldehyde | ChEBI | 1H-indol-3-Ylacetaldehyde | HMDB | 2-(3-Indolyl)acetaldehyde | HMDB | indol-3-Ylacetaldehyde | HMDB | Tryptaldehyde | HMDB |
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Chemical Formula | C10H9NO |
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Average Mass | 159.1846 Da |
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Monoisotopic Mass | 159.06841 Da |
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IUPAC Name | 2-(1H-indol-3-yl)acetaldehyde |
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Traditional Name | indole-3-acetaldehyde |
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CAS Registry Number | 2591-98-2 |
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SMILES | O=CCC1=CNC2=C1C=CC=C2 |
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InChI Identifier | InChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2 |
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InChI Key | WHOOUMGHGSPMGR-UHFFFAOYSA-N |
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Experimental Spectra |
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| Not Available | 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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| Not Available | Species |
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Species of Origin | |
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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
- Substituted pyrrole
- Benzenoid
- Alpha-hydrogen aldehyde
- Pyrrole
- Heteroaromatic compound
- Azacycle
- Aldehyde
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Organic nitrogen compound
- 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 | - Tottmar O, Hellstrom E: Aldehyde dehydrogenase in blood: a sensitive assay and inhibition by disulfiram. Pharmacol Biochem Behav. 1983;18 Suppl 1:103-7. doi: 10.1016/0091-3057(83)90154-5. [PubMed:6634824 ]
- Kumavath RN, Ramana ChV, Sasikala Ch: L-Tryptophan catabolism by Rubrivivax benzoatilyticus JA2 occurs through indole 3-pyruvic acid pathway. Biodegradation. 2010 Sep;21(5):825-32. doi: 10.1007/s10532-010-9347-y. Epub 2010 Mar 9. [PubMed:20217460 ]
- Lee JH, Kim YG, Kim CJ, Lee JC, Cho MH, Lee J: Indole-3-acetaldehyde from Rhodococcus sp. BFI 332 inhibits Escherichia coli O157:H7 biofilm formation. Appl Microbiol Biotechnol. 2012 Nov;96(4):1071-8. doi: 10.1007/s00253-012-3881-y. Epub 2012 Jan 25. [PubMed:22274708 ]
- Das PK, Guha SR: In vitro pigment formation from tryptamine. Role of indole-3-acetaldehyde. Biochem Pharmacol. 1985 Aug 1;34(15):2663-7. doi: 10.1016/0006-2952(85)90564-7. [PubMed:4015706 ]
- Nilsson GE, Tottmar O: Biogenic aldehydes in brain: characteristics of a reaction between rat brain tissue and indole-3-acetaldehyde. J Neurochem. 1985 Sep;45(3):744-51. doi: 10.1111/j.1471-4159.1985.tb04055.x. [PubMed:4031860 ]
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