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Showing Compound 1H-Indole-3-methanol (FDB000939)

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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-HydroxymethylindoleChEBI
3-IndolylcarbinolChEBI
1H-indol-3-YlmethanolHMDB
1H-Indole-3-methanolHMDB
3-(Hydroxymethyl)indoleHMDB
3-IndolecarbinolHMDB
3-IndolylmethanolHMDB
IndinolHMDB
Indole-3-methanolHMDB
I3c CPDHMDB
(1H-indol-3-yl)MethanolHMDB
Indole-3-carbinolChEBI
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 - Experimental
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
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00r5-2900000000-f67a34f5d6d03a911b8cSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-12f644dadc5182e9f9c6Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03fr-9000000000-be1a2f6d844ca724831dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-3d625989dc1eb3b60365Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fai-3900000000-456eeacfdc17f124472fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-9200000000-43d8007af2a1b33116f9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0900000000-3cbf76550dfd3aeccc0fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-6be8a0cd1ce1dba5b9e1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-3ef2bab535c991126784Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-c5a6ab59281e2cfbc98eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-0f00e06fab36aa86a8c3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-e7a17ba9d950e0fd8d89Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
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
amphiestrogenicDUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti lupus52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti metastatic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti papillomic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti proliferantDUKE
anti respiroticDUKE
anti thyroidDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
apoptoticDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cytochrome-p450 inducerDUKE
detoxicant50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
DNA-protectiveDUKE
estrogenicDUKE
genotoxic50902 A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
mutagenicDUKE
NF-kappa-B inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
quinone-reductase inducerDUKE
tumor promoter50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.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).