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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2007-01-22 13:00:01 UTC

Update Date

2023-02-21 17:17:07 UTC

HMDB ID

HMDB0005785

Secondary Accession Numbers

HMDB05785

Metabolite Identification

Common Name

Indole-3-carbinol

Description

Indole-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Hydroxymethylindole	ChEBI
3-Indolylcarbinol	ChEBI
1H-Indole-3-methanol	MeSH
I3c CPD	MeSH
Indole-3-methanol	MeSH
1H-indol-3-Ylmethanol	HMDB
3-(Hydroxymethyl)indole	HMDB
3-Indolecarbinol	HMDB
3-Indolylmethanol	HMDB
Indinol	HMDB
Indole-3-carbinol	ChEBI
(1H-Indol-3-yl)methanol	HMDB

Chemical Formula

C₉H₉NO

Average Molecular Weight

147.1739

Monoisotopic Molecular Weight

147.068413915

IUPAC Name

(1H-indol-3-yl)methanol

Traditional Name

indole-3-carbinol

CAS Registry Number

700-06-1

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 Key

IVYPNXXAYMYVSP-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolyl alcohol (CHEBI:24814 )
an indole-phytolexin (CPDQT-428 )

Ontology

Not Available

Urine (PMID: 31235863)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005785)

Source

Exogenous

Food

Food (HMDB: HMDB0005785)

Vegetable

Cabbage

Brassica

Brassicas (FooDB: FOOD00857)

Endogenous

Plant

Plant (HMDB: HMDB0005785)

Process

Not Available

Role

Biological role

Amphiestrogenic (HMDB: HMDB0005785)
Anti cancer (HMDB: HMDB0005785)
Anti-estrogenic (HMDB: HMDB0005785)
Anti-inflammatory (HMDB: HMDB0005785)
Anti lupus (HMDB: HMDB0005785)
Anti metastatic (HMDB: HMDB0005785)
Anti papillomic (HMDB: HMDB0005785)
Anti proliferant (HMDB: HMDB0005785)
Anti respirotic (HMDB: HMDB0005785)
Anti thyroid (HMDB: HMDB0005785)
Carcinogenic (HMDB: HMDB0005785)
Cytochrome-p450 inducer (HMDB: HMDB0005785)
Detoxicant (HMDB: HMDB0005785)
DNA-protective (HMDB: HMDB0005785)
Estrogenic (HMDB: HMDB0005785)
Genotoxin (HMDB: HMDB0005785)
Mutagenic (HMDB: HMDB0005785)
Quinone-reductase inducer (HMDB: HMDB0005785)
Tumor promoter (HMDB: HMDB0005785)

Modulator

Apoptotic (HMDB: HMDB0005785)
Nitric-oxide inhibitor (HMDB: HMDB0005785)

Inhibitor

Enzyme inhibitor

NF-kappa-B inhibitor (HMDB: HMDB0005785)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0005785)
Cancer preventive (HMDB: HMDB0005785)

Hepatoprotective (HMDB: HMDB0005785)
Pharmaceutical (HMDB: HMDB0005785)

Antineoplastic agent (HMDB: HMDB0005785)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	90 °C	Not Available
Boiling Point	360.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	8339 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.366 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.75 g/L	ALOGPS
logP	1.66	ALOGPS
logP	1.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	15.1	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	36.02 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	43.96 m³·mol⁻¹	ChemAxon
Polarizability	15.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	131.493	31661259
DarkChem	[M-H]-	128.318	31661259
DeepCCS	[M+H]+	129.567	30932474
DeepCCS	[M-H]-	125.967	30932474
DeepCCS	[M-2H]-	163.346	30932474
DeepCCS	[M+Na]+	138.482	30932474
AllCCS	[M+H]+	130.8	32859911
AllCCS	[M+H-H2O]+	126.1	32859911
AllCCS	[M+NH4]+	135.2	32859911
AllCCS	[M+Na]+	136.5	32859911
AllCCS	[M-H]-	130.1	32859911
AllCCS	[M+Na-2H]-	131.0	32859911
AllCCS	[M+HCOO]-	132.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-carbinol	OCC1=CNC2=C1C=CC=C2	2944.1	Standard polar	33892256
Indole-3-carbinol	OCC1=CNC2=C1C=CC=C2	1642.5	Standard non polar	33892256
Indole-3-carbinol	OCC1=CNC2=C1C=CC=C2	1674.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-carbinol,1TMS,isomer #1	C[Si](C)(C)OCC1=C[NH]C2=CC=CC=C12	1724.7	Semi standard non polar	33892256
Indole-3-carbinol,1TMS,isomer #2	C[Si](C)(C)N1C=C(CO)C2=CC=CC=C21	1751.7	Semi standard non polar	33892256
Indole-3-carbinol,2TMS,isomer #1	C[Si](C)(C)OCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1777.9	Semi standard non polar	33892256
Indole-3-carbinol,2TMS,isomer #1	C[Si](C)(C)OCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1784.8	Standard non polar	33892256
Indole-3-carbinol,2TMS,isomer #1	C[Si](C)(C)OCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1856.5	Standard polar	33892256
Indole-3-carbinol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=C[NH]C2=CC=CC=C12	1990.3	Semi standard non polar	33892256
Indole-3-carbinol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CO)C2=CC=CC=C21	2001.8	Semi standard non polar	33892256
Indole-3-carbinol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2225.8	Semi standard non polar	33892256
Indole-3-carbinol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2202.8	Standard non polar	33892256
Indole-3-carbinol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2129.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-carbinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-015a-0900000000-d9bdc5ba99fd6227768b	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-carbinol GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9530000000-48825a883c035797c55f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-carbinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-carbinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carbinol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00r5-2900000000-f67a34f5d6d03a911b8c	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carbinol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-9000000000-12f644dadc5182e9f9c6	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carbinol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-03fr-9000000000-be1a2f6d844ca724831d	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carbinol LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-3d625989dc1eb3b60365	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carbinol LC-ESI-QTOF , positive-QTOF	splash10-0fai-3900000000-456eeacfdc17f124472f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carbinol LC-ESI-QTOF , positive-QTOF	splash10-004i-9200000000-43d8007af2a1b33116f9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indole-3-carbinol 35V, Positive-QTOF	splash10-0a4i-1900000000-dbcb3abd4a9eaf9096a4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 10V, Positive-QTOF	splash10-000t-0900000000-3cbf76550dfd3aeccc0f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 20V, Positive-QTOF	splash10-001i-0900000000-6be8a0cd1ce1dba5b9e1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 40V, Positive-QTOF	splash10-001i-0900000000-3ef2bab535c991126784	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 10V, Negative-QTOF	splash10-0002-0900000000-c5a6ab59281e2cfbc98e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 20V, Negative-QTOF	splash10-014i-0900000000-0f00e06fab36aa86a8c3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 40V, Negative-QTOF	splash10-014i-1900000000-e7a17ba9d950e0fd8d89	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 10V, Negative-QTOF	splash10-00mk-0900000000-cebd396bcbd40c0432ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 20V, Negative-QTOF	splash10-014i-0900000000-93800e2e7b5e269d361d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 40V, Negative-QTOF	splash10-014i-0900000000-89c3f30c8225ba6d5d62	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 10V, Positive-QTOF	splash10-001i-0900000000-1642190860f519e20beb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 20V, Positive-QTOF	splash10-001i-1900000000-291e3bc880f12fd60663	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-carbinol 40V, Positive-QTOF	splash10-0ufr-7900000000-6fb21bd39ff84a32d974	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	31235863	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB12881

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000939

KNApSAcK ID

C00041598

Chemspider ID

3581

KEGG Compound ID

Not Available

BioCyc ID

CPDQT-428

BiGG ID

Not Available

Wikipedia Link

Indole-3-carbinol

METLIN ID

Not Available

PubChem Compound

3712

PDB ID

Not Available

ChEBI ID

24814

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1448011

References

Synthesis Reference

Leete, 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

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 ]
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 ]
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

Enzyme Details

1. Aryl hydrocarbon receptor

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

Showing metabocard for Indole-3-carbinol (HMDB0005785)

MOL for HMDB0005785 (Indole-3-carbinol)

3D MOL for HMDB0005785 (Indole-3-carbinol)

3D SDF for HMDB0005785 (Indole-3-carbinol)

3D-SDF for HMDB0005785 (Indole-3-carbinol)

PDB for HMDB0005785 (Indole-3-carbinol)

3D PDB for HMDB0005785 (Indole-3-carbinol)

SMILES for HMDB0005785 (Indole-3-carbinol)

INCHI for HMDB0005785 (Indole-3-carbinol)

Structure for HMDB0005785 (Indole-3-carbinol)

3D Structure for HMDB0005785 (Indole-3-carbinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes