| 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 |
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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 | 2012-07-25 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-9000000000-12f644dadc5182e9f9c6 | 2012-07-25 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-03fr-9000000000-be1a2f6d844ca724831d | 2012-07-25 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001i-0900000000-3d625989dc1eb3b60365 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0fai-3900000000-456eeacfdc17f124472f | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004i-9200000000-43d8007af2a1b33116f9 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0a4i-1900000000-dbcb3abd4a9eaf9096a4 | 2021-09-20 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000t-0900000000-3cbf76550dfd3aeccc0f | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-6be8a0cd1ce1dba5b9e1 | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-0900000000-3ef2bab535c991126784 | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-c5a6ab59281e2cfbc98e | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-0f00e06fab36aa86a8c3 | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-1900000000-e7a17ba9d950e0fd8d89 | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00mk-0900000000-cebd396bcbd40c0432ff | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-93800e2e7b5e269d361d | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-0900000000-89c3f30c8225ba6d5d62 | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-1642190860f519e20beb | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-1900000000-291e3bc880f12fd60663 | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ufr-7900000000-6fb21bd39ff84a32d974 | 2021-09-24 | View Spectrum |
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| NMR | | Type | Description | | View |
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| 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, experimental) | | Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | | Spectrum |
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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 | | Descriptor | ID | Definition | Reference |
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| Amphiestrogenic | | An agent that exhibits both estrogenic and anti-estrogenic properties, depending on the tissue type. It plays a role in regulating hormonal balance and has therapeutic applications in managing menopausal symptoms, osteoporosis, and certain types of cancer, such as breast and endometrial cancer. | DUKE | | Anti-cancer | 35610 | An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival. | DUKE | | Anti estrogenic | 35222 | An agent that blocks or reduces estrogen's effects, used to treat hormone-sensitive cancers, such as breast cancer, and manage conditions like endometriosis and uterine fibroids, by inhibiting estrogen's biological role in promoting cell growth. | DUKE | | Anti-inflammatory | 35472 | An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis. | DUKE | | Anti-lupus | 52217 | An agent that suppresses the immune system, reducing inflammation and autoimmune responses, commonly used to manage systemic lupus erythematosus (SLE) and other autoimmune disorders. | DUKE | | Anti metastatic | 35610 | An agent that inhibits cancer cell spread, reducing tumor metastasis. It plays a biological role in blocking cell migration and invasion, and has therapeutic applications in cancer treatment. Key medical uses include preventing cancer recurrence and improving survival rates in patients with various types of cancer. | DUKE | | Anti-papillomic | 22587 | An agent that targets and inhibits the formation of papillomas, reducing the growth of abnormal cells. Therapeutically, it is used to treat and prevent human papillomavirus (HPV) related diseases, such as cervical cancer and genital warts, by boosting the immune system to fight off the virus. | DUKE | | Anti proliferant | | An agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation. | DUKE | | Anti-respirotic | | An agent that inhibits respirosis, a process of cellular damage caused by mitochondrial dysfunction. It plays a biological role in protecting cells from oxidative stress. Therapeutically, anti-respirotics have applications in managing neurodegenerative diseases, such as Alzheimer's and Parkinson's, and key medical uses include treating conditions related to mitochondrial damage and dysfunction. | DUKE | | Anti-thyroid | | An agent that inhibits thyroid hormone production, used to treat hyperthyroidism by reducing thyroid hormone levels, commonly applied in managing conditions like Graves' disease. | DUKE | | Antitumor | 35610 | An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes. | DUKE | | Apoptotic | | An agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy. | DUKE | | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | | Carcinogenic | 50903 | An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment. | DUKE | | Chemopreventive | 35610 | An agent that prevents or delays the development of cancer, reducing the risk of tumor formation and progression. It plays a biological role in inhibiting carcinogenesis, and has therapeutic applications in cancer prevention, with key medical uses including reducing the risk of colorectal, breast, and prostate cancers. | DUKE | | Cytochrome-p450 inducer | | An agent that stimulates cytochrome-p450 enzyme activity, enhancing drug metabolism. Therapeutically, it increases clearance of toxic substances and certain medications, with applications in managing drug interactions, toxic exposures, and some cancers. | DUKE | | Detoxicant | 50247 | An agent that facilitates the removal of toxins from the body, playing a crucial role in reducing oxidative stress and inflammation. Therapeutically, detoxicants are used to treat poisoning, heavy metal exposure, and liver diseases, promoting overall health and well-being by neutralizing harmful substances. | DUKE | | DNA-protective | | An agent that prevents or repairs DNA damage, playing a crucial role in maintaining genomic stability. Therapeutically, it has applications in cancer prevention, neuroprotection, and anti-aging. Key medical uses include reducing chemotherapy-induced DNA damage and mitigating radiation exposure effects. | DUKE | | Estrogenic | | An agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility. | DUKE | | Genotoxic | 50902 | An agent that damages genetic material, disrupting DNA structure and function. It has a biological role in inducing mutations and cancer. Therapeutically, genotoxic agents are used in chemotherapy to target rapidly dividing cancer cells. Key medical uses include cancer treatment, with applications in oncology for killing malignant cells and inhibiting tumor growth. | DUKE | | Hepatoprotective | 62868 | An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities. | DUKE | | Mutagenic | | An agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research. | DUKE | | NF-kappa-B inhibitor | 35222 | An agent that blocks the activity of NF-kappa-B, a protein complex involved in inflammation and immune responses, reducing inflammation and cell proliferation. Therapeutically, it is used to treat conditions such as cancer, autoimmune disorders, and inflammatory diseases, including rheumatoid arthritis and asthma. | DUKE | | Nitric-oxide inhibitor | 35222 | An agent that blocks the production of nitric oxide, reducing inflammation and vascular relaxation. Therapeutically, it's used to treat conditions like hypertension, angina, and septic shock, by constricting blood vessels and improving blood pressure. Key medical uses include cardiovascular and critical care applications. | DUKE | | Quinone-reductase inducer | | An agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases. | DUKE | | Tumor promoter | 50903 | A substance that enhances the growth and proliferation of cancer cells, often used in research to study cancer development. Therapeutically, understanding tumor promoters informs cancer prevention and treatment strategies, with applications in oncology for developing targeted therapies to inhibit tumor growth and progression. | DUKE |
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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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