Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 12:54:54 PM |
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Metabolite ID | PAMDB120247 |
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Identification |
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Name: |
indole-3-acetonitrile |
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Description: | A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group. |
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Structure |
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Synonyms: | - (indol-3-yl)acetonitrile
- (Indol-3-yl)acetonitrile
- (Indole-3-yl)acetonitrile
- 3-(cyanomethyl)indole
- 3-Indoleacetonitrile
- 3-indolylacetonitrile
- Indol-3-ylacetonitrile
- Indole-3-acetonitrile
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Chemical Formula: |
C10H8N2 |
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Average Molecular Weight: |
156.187 |
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Monoisotopic Molecular
Weight: |
156.06874 |
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InChI Key: |
DMCPFOBLJMLSNX-UHFFFAOYSA-N |
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InChI: | InChI=1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2 |
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CAS
number: |
771-51-7 |
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IUPAC Name: | 1H-indol-3-ylacetonitrile |
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Traditional IUPAC Name: |
indole-3-acetonitrile |
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SMILES: | C2(NC1(C=CC=CC=1C(CC#N)=2)) |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities known as 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position. |
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Kingdom |
Chemical entities |
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Super Class | Organic compounds |
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Class |
Organoheterocyclic compounds |
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Sub Class | Indoles and derivatives |
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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
- Nitrile
- Carbonitrile
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen 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: |
Solid |
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Charge: | 0 |
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Melting point: |
35 - 37 °C |
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Experimental Properties: |
Property | Value | Reference |
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Melting Point | 35 - 37 °C | 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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Biological Properties |
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Cellular Locations: |
Not Available |
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Reactions: | |
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Pathways: |
- indole-3-acetate biosynthesis IV (bacteria)PWY-5025
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Spectra |
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Spectra: |
Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-004i-2950000000-640d53401ab5b06bad68 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0900000000-686ec8d86a82008f6a87 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0900000000-0f41c00c3703e04901e8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000x-1900000000-144022b6dfec80ddd4a3 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0900000000-686ec8d86a82008f6a87 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0900000000-0f41c00c3703e04901e8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000x-1900000000-144022b6dfec80ddd4a3 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-9b52919ba61c73ce0ade | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-f8b24a877c386d550c92 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-1900000000-fc82dffe3b09577e06ee | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-9b52919ba61c73ce0ade | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-f8b24a877c386d550c92 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-1900000000-fc82dffe3b09577e06ee | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-2900000000-be863c7acf7363ffeedc | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available |
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1D NMR | 13C NMR Spectrum | Not Available |
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References |
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References: |
- Pedras MS, Nycholat CM, Montaut S, Xu Y, Khan AQ (2002)Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. Phytochemistry 59, Pubmed: 11867093
- Michnovicz JJ, Bradlow HL (1990)Induction of estradiol metabolism by dietary indole-3-carbinol in humans. Journal of the National Cancer Institute 82, Pubmed: 2342128
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Synthesis Reference: |
Ahmad, A.; Spenser, Ian D. 3-Indolepyruvic acid oxime as the precursor of 3-indoleacetonitrile. Canadian Journal of Chemistry (1960), 38 1625-34. |
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Material Safety Data Sheet (MSDS) |
Download (PDF) |
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Links |
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External Links: |
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