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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-01-22 13:00:01 UTC
Update Date2023-02-21 17:17:07 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 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
Thumb
Synonyms
ValueSource
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
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point90 °CNot Available
Boiling Point360.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility8339 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.366 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB000939
KNApSAcK IDC00041598
Chemspider ID3581
KEGG Compound IDNot Available
BioCyc IDCPDQT-428
BiGG IDNot Available
Wikipedia LinkIndole-3-carbinol
METLIN IDNot Available
PubChem Compound3712
PDB IDNot Available
ChEBI ID24814
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1448011
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)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. Rogan EG: The natural chemopreventive compound indole-3-carbinol: state of the science. In Vivo. 2006 Mar-Apr;20(2):221-8. [PubMed:16634522 ]

Enzymes

General function:
Involved in transcription regulator activity
Specific function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular weight:
96146.7