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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2007-01-22 13:00:01 UTC
Update Date2020-01-28 17:25:54 UTC
HMDB IDHMDB0005785
Secondary Accession Numbers
  • HMDB05785
Metabolite Identification
Common NameIndole-3-carbinol
DescriptionIndole-3-carbinol, also known as 3-indolylcarbinol or 1H-indole-3-methanol, 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. Indole-3-carbinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Indole-3-carbinol is a dietary indole present in cruciferous vegetables that has been shown to influence estradiol metabolism in humans and may provide a new chemopreventive approach to estrogen-dependent diseases (PMID: 2342128 ). Indole-3-carbinol is produced by members of the family Cruciferae, particularly members of the genus Brassica (e.g. cabbage, radishes, cauliflower, broccoli, Brussels sprouts, and daikon). Indole-3-carbinol is metabolized into 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; it can suppress the proliferation of certain cancer cells, including breast cancer, prostate cancer, endometrial cancer, colon cancer, and leukemic cells (PMID: 16634522 , 16082211 ).
Structure
Data?1580160447
Synonyms
ValueSource
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
Indole-3-carbinolChEBI
(1H-Indol-3-yl)methanolHMDB
Chemical FormulaC9H9NO
Average Molecular Weight147.1739
Monoisotopic Molecular Weight147.068413915
IUPAC Name(1H-indol-3-yl)methanol
Traditional Nameindole-3-carbinol
CAS Registry Number700-06-1
SMILES
OCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
InChI KeyIVYPNXXAYMYVSP-UHFFFAOYSA-N
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point90 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-015a-0900000000-d9bdc5ba99fd6227768bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9530000000-48825a883c035797c55fJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00r5-2900000000-f67a34f5d6d03a911b8cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-12f644dadc5182e9f9c6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03fr-9000000000-be1a2f6d844ca724831dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-3d625989dc1eb3b60365JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fai-3900000000-456eeacfdc17f124472fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-9200000000-43d8007af2a1b33116f9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0900000000-3cbf76550dfd3aeccc0fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-6be8a0cd1ce1dba5b9e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-3ef2bab535c991126784JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-c5a6ab59281e2cfbc98eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-0f00e06fab36aa86a8c3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-e7a17ba9d950e0fd8d89JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12881
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000939
KNApSAcK IDNot Available
Chemspider ID3581
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndole-3-carbinol
METLIN IDNot Available
PubChem Compound3712
PDB IDNot Available
ChEBI ID24814
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceLeete, Edward; Marion, Leo. Hydrogenolysis of 3-(hydroxymethyl)indole and other indole derivatives with lithium aluminum hydride. Canadian Journal of Chemistry (1953), 31 775-84.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Aggarwal BB, Ichikawa H: Molecular targets and anticancer potential of indole-3-carbinol and its derivatives. Cell Cycle. 2005 Sep;4(9):1201-15. Epub 2005 Sep 6. [PubMed:16082211 ]
  2. Rogan EG: The natural chemopreventive compound indole-3-carbinol: state of the science. In Vivo. 2006 Mar-Apr;20(2):221-8. [PubMed:16634522 ]
  3. Michnovicz JJ, Bradlow HL: Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst. 1990 Jun 6;82(11):947-9. [PubMed:2342128 ]