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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-01-22 13:00:01 UTC
Update Date2021-10-13 04:47:22 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
Data?1588172706
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
Disposition

Biological location

Source

Route of exposure

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
PropertyValueSource
Water Solubility3.75 g/LALOGPS
logP10(1.66) g/LALOGPS
logP10(1.3) g/LChemAxon
logS10(-1.6) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.49331661259
DarkChem[M-H]-128.31831661259
DeepCCS[M+H]+129.56730932474
DeepCCS[M-H]-125.96730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Indole-3-carbinolOCC1=CNC2=C1C=CC=C22944.1Standard polar33892256
Indole-3-carbinolOCC1=CNC2=C1C=CC=C21642.5Standard non polar33892256
Indole-3-carbinolOCC1=CNC2=C1C=CC=C21674.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indole-3-carbinol,1TMS,isomer #1C[Si](C)(C)OCC1=C[NH]C2=CC=CC=C121724.7Semi standard non polar33892256
Indole-3-carbinol,1TMS,isomer #2C[Si](C)(C)N1C=C(CO)C2=CC=CC=C211751.7Semi standard non polar33892256
Indole-3-carbinol,2TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C2=CC=CC=C121777.9Semi standard non polar33892256
Indole-3-carbinol,2TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C2=CC=CC=C121784.8Standard non polar33892256
Indole-3-carbinol,2TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C2=CC=CC=C121856.5Standard polar33892256
Indole-3-carbinol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=C[NH]C2=CC=CC=C121990.3Semi standard non polar33892256
Indole-3-carbinol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CO)C2=CC=CC=C212001.8Semi standard non polar33892256
Indole-3-carbinol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122225.8Semi standard non polar33892256
Indole-3-carbinol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122202.8Standard non polar33892256
Indole-3-carbinol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122129.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-carbinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-015a-0900000000-d9bdc5ba99fd6227768b2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-carbinol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9530000000-48825a883c035797c55f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-carbinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-carbinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carbinol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00r5-2900000000-f67a34f5d6d03a911b8c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carbinol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0006-9000000000-12f644dadc5182e9f9c62012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carbinol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-03fr-9000000000-be1a2f6d844ca724831d2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carbinol LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-3d625989dc1eb3b603652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carbinol LC-ESI-QTOF , positive-QTOFsplash10-0fai-3900000000-456eeacfdc17f124472f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carbinol LC-ESI-QTOF , positive-QTOFsplash10-004i-9200000000-43d8007af2a1b33116f92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-carbinol 35V, Positive-QTOFsplash10-0a4i-1900000000-dbcb3abd4a9eaf9096a42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 10V, Positive-QTOFsplash10-000t-0900000000-3cbf76550dfd3aeccc0f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 20V, Positive-QTOFsplash10-001i-0900000000-6be8a0cd1ce1dba5b9e12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 40V, Positive-QTOFsplash10-001i-0900000000-3ef2bab535c9911267842017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 10V, Negative-QTOFsplash10-0002-0900000000-c5a6ab59281e2cfbc98e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 20V, Negative-QTOFsplash10-014i-0900000000-0f00e06fab36aa86a8c32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 40V, Negative-QTOFsplash10-014i-1900000000-e7a17ba9d950e0fd8d892017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 10V, Negative-QTOFsplash10-00mk-0900000000-cebd396bcbd40c0432ff2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 20V, Negative-QTOFsplash10-014i-0900000000-93800e2e7b5e269d361d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 40V, Negative-QTOFsplash10-014i-0900000000-89c3f30c8225ba6d5d622021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 10V, Positive-QTOFsplash10-001i-0900000000-1642190860f519e20beb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 20V, Positive-QTOFsplash10-001i-1900000000-291e3bc880f12fd606632021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-carbinol 40V, Positive-QTOFsplash10-0ufr-7900000000-6fb21bd39ff84a32d9742021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
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)Download (PDF)
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 ]