Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:46 UTC |
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Update date | 2019-11-26 02:55:39 UTC |
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Primary ID | FDB000939 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 1H-Indole-3-methanol |
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Description | Produced from glucosinolates in Brassica species on crushing or cooking. Potential nutriceutical
16082211).; Indole-3-carbinol is produced by members of the family Cruciferae and particularly members of the genus Brassica, for example, cabbage, radishes, cauliflower, broccoli, Brussels sprouts, and daikon). Indole-3-carbinol is metabolized to a number of products, including the dimeric 3,3'-diindolylmethane. Both 3,3'-diindolylmethane and Indole-3-carbinol are thought to have biological effects. Indole-3-carbinol is a natural chemopreventive compound. It has multiple anticarcinogenic and antitumorigenic properties by suppressing the proliferation of certain cancer cells, including breast cancer, prostate cancer, endometrial cancer, colon cancer, and leukemic cells (PMID: 16634522. 1H-Indole-3-methanol is found in many foods, some of which are broccoli, brassicas, cabbage, and brussel sprouts. |
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CAS Number | 700-06-1 |
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Structure | |
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Synonyms | Synonym | Source |
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3-Hydroxymethylindole | ChEBI | 3-Indolylcarbinol | ChEBI | 1H-Indole-3-methanol | MeSH | I3c CPD | MeSH | Indole-3-methanol | MeSH | 1H-indol-3-Ylmethanol | HMDB | 3-(Hydroxymethyl)indole | HMDB | 3-Indolecarbinol | HMDB | 3-Indolylmethanol | HMDB | Indinol | HMDB | Indole-3-carbinol | ChEBI | (1H-Indol-3-yl)methanol | HMDB | 1H-indol-3-ylmethanol | biospider | 1H-Indole-3-methanol (9CI) | biospider | 3-Indolemethanol | biospider | 3-indolylcarbinol | biospider | C9H9NO | biospider | I3C cpd | biospider | indole-3-methanol | biospider | PREVENTION 4 (INDOLE-3-CARBINOL) | biospider |
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Predicted Properties | |
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Chemical Formula | C9H9NO |
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IUPAC name | (1H-indol-3-yl)methanol |
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InChI Identifier | InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2 |
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InChI Key | IVYPNXXAYMYVSP-UHFFFAOYSA-N |
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Isomeric SMILES | OCC1=CNC2=CC=CC=C12 |
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Average Molecular Weight | 147.1739 |
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Monoisotopic Molecular Weight | 147.068413915 |
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Classification |
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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
- Pyrrole
- Heteroaromatic compound
- Azacycle
- Alcohol
- Hydrocarbon derivative
- Organopnictogen compound
- Aromatic alcohol
- Organic oxygen compound
- Organic nitrogen compound
- Primary alcohol
- Organooxygen compound
- Organonitrogen 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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Disposition | Route of exposure: Source: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 73.45%; H 6.16%; N 9.52%; O 10.87% | DFC |
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Melting Point | Mp 158° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | pKa1 16.5 (25°,NH, KOH aq.) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | 1H-Indole-3-methanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-015a-0900000000-d9bdc5ba99fd6227768b | Spectrum | Predicted GC-MS | 1H-Indole-3-methanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-9530000000-48825a883c035797c55f | Spectrum | Predicted GC-MS | 1H-Indole-3-methanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 1H-Indole-3-methanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00r5-2900000000-f67a34f5d6d03a911b8c | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-9000000000-12f644dadc5182e9f9c6 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-03fr-9000000000-be1a2f6d844ca724831d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001i-0900000000-3d625989dc1eb3b60365 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0fai-3900000000-456eeacfdc17f124472f | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004i-9200000000-43d8007af2a1b33116f9 | Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0a4i-1900000000-dbcb3abd4a9eaf9096a4 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000t-0900000000-3cbf76550dfd3aeccc0f | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-6be8a0cd1ce1dba5b9e1 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-0900000000-3ef2bab535c991126784 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-c5a6ab59281e2cfbc98e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-0f00e06fab36aa86a8c3 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-1900000000-e7a17ba9d950e0fd8d89 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00mk-0900000000-cebd396bcbd40c0432ff | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-93800e2e7b5e269d361d | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-0900000000-89c3f30c8225ba6d5d62 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-1642190860f519e20beb | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-1900000000-291e3bc880f12fd60663 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ufr-7900000000-6fb21bd39ff84a32d974 | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 3581 |
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ChEMBL ID | CHEMBL155625 |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 3712 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 24814 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB05785 |
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CRC / DFC (Dictionary of Food Compounds) ID | BND53-C:BND53-C |
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EAFUS ID | Not Available |
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Dr. Duke ID | INDOLE-3-CARBINOL |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Indole-3-carbinol |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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