Record Information
Version1.0
Creation date2010-04-08 22:04:46 UTC
Update date2019-11-26 02:55:39 UTC
Primary IDFDB000939
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1H-Indole-3-methanol
DescriptionProduced 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.
CAS Number700-06-1
Structure
Thumb
Synonyms
SynonymSource
3-HydroxymethylindoleChEBI
3-IndolylcarbinolChEBI
1H-Indole-3-methanolMeSH
I3c CPDMeSH
Indole-3-methanolMeSH
1H-indol-3-YlmethanolHMDB
3-(Hydroxymethyl)indoleHMDB
3-IndolecarbinolHMDB
3-IndolylmethanolHMDB
IndinolHMDB
Indole-3-carbinolChEBI
(1H-Indol-3-yl)methanolHMDB
1H-indol-3-ylmethanolbiospider
1H-Indole-3-methanol (9CI)biospider
3-Indolemethanolbiospider
3-indolylcarbinolbiospider
C9H9NObiospider
I3C cpdbiospider
indole-3-methanolbiospider
PREVENTION 4 (INDOLE-3-CARBINOL)biospider
Predicted Properties
PropertyValueSource
Water Solubility3.75 g/LALOGPS
logP1.66ALOGPS
logP1.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)15.1ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.96 m³·mol⁻¹ChemAxon
Polarizability15.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H9NO
IUPAC name(1H-indol-3-yl)methanol
InChI IdentifierInChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
InChI KeyIVYPNXXAYMYVSP-UHFFFAOYSA-N
Isomeric SMILESOCC1=CNC2=CC=CC=C12
Average Molecular Weight147.1739
Monoisotopic Molecular Weight147.068413915
Classification
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 73.45%; H 6.16%; N 9.52%; O 10.87%DFC
Melting PointMp 158°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa1 16.5 (25°,NH, KOH aq.)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1H-Indole-3-methanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-015a-0900000000-d9bdc5ba99fd6227768bSpectrum
Predicted GC-MS1H-Indole-3-methanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9530000000-48825a883c035797c55fSpectrum
Predicted GC-MS1H-Indole-3-methanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1H-Indole-3-methanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00r5-2900000000-f67a34f5d6d03a911b8c2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-12f644dadc5182e9f9c62012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03fr-9000000000-be1a2f6d844ca724831d2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-3d625989dc1eb3b603652017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fai-3900000000-456eeacfdc17f124472f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-9200000000-43d8007af2a1b33116f92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-1900000000-dbcb3abd4a9eaf9096a42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0900000000-3cbf76550dfd3aeccc0f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-6be8a0cd1ce1dba5b9e12017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-3ef2bab535c9911267842017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-c5a6ab59281e2cfbc98e2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-0f00e06fab36aa86a8c32017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-e7a17ba9d950e0fd8d892017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00mk-0900000000-cebd396bcbd40c0432ff2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-93800e2e7b5e269d361d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-89c3f30c8225ba6d5d622021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-1642190860f519e20beb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-291e3bc880f12fd606632021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-7900000000-6fb21bd39ff84a32d9742021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID3581
ChEMBL IDCHEMBL155625
KEGG Compound IDNot Available
Pubchem Compound ID3712
Pubchem Substance IDNot Available
ChEBI ID24814
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05785
CRC / DFC (Dictionary of Food Compounds) IDBND53-C:BND53-C
EAFUS IDNot Available
Dr. Duke IDINDOLE-3-CARBINOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDIndole-3-carbinol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
AmphiestrogenicAn 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-cancer35610 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 estrogenic35222 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-inflammatory35472 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-lupus52217 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 metastatic35610 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-papillomic22587 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 proliferantAn 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-respiroticAn 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-thyroidAn agent that inhibits thyroid hormone production, used to treat hyperthyroidism by reducing thyroid hormone levels, commonly applied in managing conditions like Graves' disease.DUKE
Antitumor35610 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
ApoptoticAn 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 preventive35610 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
Carcinogenic50903 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
Chemopreventive35610 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 inducerAn 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
Detoxicant50247 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-protectiveAn 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
EstrogenicAn 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
Genotoxic50902 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
Hepatoprotective62868 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
MutagenicAn 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 inhibitor35222 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 inhibitor35222 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 inducerAn 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 promoter50903 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).