AFCDB: 1H-Indole-3-methanol (FDB000939)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:46 UTC

Update date

2019-11-26 02:55:39 UTC

Primary ID

FDB000939

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

1H-Indole-3-methanol

Description

Produced 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 Number

700-06-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted 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

Chemical Formula

C9H9NO

IUPAC name

(1H-indol-3-yl)methanol

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

Isomeric SMILES

OCC1=CNC2=CC=CC=C12

Average Molecular Weight

147.1739

Monoisotopic Molecular Weight

147.068413915

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.

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 73.45%; H 6.16%; N 9.52%; O 10.87%	DFC
Melting Point	Mp 158°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	pKa1 16.5 (25°,NH, KOH aq.)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	1H-Indole-3-methanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-015a-0900000000-d9bdc5ba99fd6227768b	Spectrum
Predicted GC-MS	1H-Indole-3-methanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9530000000-48825a883c035797c55f	Spectrum
Predicted GC-MS	1H-Indole-3-methanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1H-Indole-3-methanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

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

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

External Links

ChemSpider ID

3581

ChEMBL ID

CHEMBL155625

KEGG Compound ID

Not Available

Pubchem Compound ID

3712

Pubchem Substance ID

Not Available

ChEBI ID

24814

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05785

CRC / DFC (Dictionary of Food Compounds) ID

BND53-C:BND53-C

EAFUS ID

Not Available

Dr. Duke ID

INDOLE-3-CARBINOL

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Indole-3-carbinol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
amphiestrogenic			DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti estrogenic	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti lupus	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti metastatic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti papillomic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti proliferant			DUKE
anti respirotic			DUKE
anti thyroid			DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
apoptotic			DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
carcinogenic	50903	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
chemopreventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cytochrome-p450 inducer			DUKE
detoxicant	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
DNA-protective			DUKE
estrogenic			DUKE
genotoxic	50902	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
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
mutagenic			DUKE
NF-kappa-B inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
nitric-oxide inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
quinone-reductase inducer			DUKE
tumor promoter	50903	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

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

1H-Indole-3-methanol (FDB000939)

Structure for FDB000939 (1H-Indole-3-methanol)