SKATOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H9N
Molecular Weight	131.1745
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CNC2=C1C=CC=C2

InChI

InChIKey=ZFRKQXVRDFCRJG-UHFFFAOYSA-N

InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3

HIDE SMILES / InChI

Molecular Formula	C9H9N
Molecular Weight	131.1745
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27138278
Curator's Comment: Description was created based on several sources, including http://twodrugs.com/dict/skatole.html and http://www.thegoodscentscompany.com/data/rw1006331.html

Skatole or 3-methylindole is a mildly toxic white crystalline organic compound belonging to the indole family. It is formed in the intestine by the bacterial decomposition of l-tryptophan and found in fecal matter, to which it imparts its characteristic odor. Skatole is a partial AhR agonist. Skatole is used in perfume compositions and in artificial Civet bases.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Aryl hydrocarbon receptor 27 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27138278	Partial Agonist 297
Protein synthesis 4 Target ID: Protein synthesis Sources: https://www.ncbi.nlm.nih.gov/pubmed/7495379	Inhibitor 8504	0.024 mM [EC50]
cytochrome P450 2A19 2 Target ID: 403149.0 Gene Symbol: CYP2A19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17908921	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Solvent effects on the fluorescence quenching of tryptophan by amides via electron transfer. Experimental and computational studies.	2009-03-05	18672928
Fe(III) stimulates 3-methylindole and 4-methylphenol production in swine lagoon enrichments and Clostridium scatologenes ATCC 25775.	2009-01	19055633
3-Methylindole production is regulated in Clostridium scatologenes ATCC 25775.	2009-01	19055631
Design, structure-activity relationships, X-ray crystal structure, and energetic contributions of a critical P1 pharmacophore: 3-chloroindole-7-yl-based factor Xa inhibitors.	2008-12-11	18998662
The chromatin remodeler SPLAYED regulates specific stress signaling pathways.	2008-12	19079584
Carbohydrate-protein recognition probed by density functional theory and ab initio calculations including dispersive interactions.	2008-11-21	18979035
Mechanism of the efficient tryptophan fluorescence quenching in human gammaD-crystallin studied by time-resolved fluorescence.	2008-10-07	18795792
Single mutations change CYP2F3 from a dehydrogenase of 3-methylindole to an oxygenase.	2008-09-16	18717595
Reverse and conventional chemical ecology approaches for the development of oviposition attractants for Culex mosquitoes.	2008-08-22	18725946
Gene expression profiles in liver of pigs with extreme high and low levels of androstenone.	2008-08-06	18684314
Effect of ginkgo biloba and dexamethasone in the treatment of 3-methylindole-induced anosmia mouse model.	2008-07-01	18588762
L-tryptophan radical cation electron spin resonance studies: connecting solution-derived hyperfine coupling constants with protein spectral interpretations.	2008-05-21	18433127
Field sampling method for quantifying odorants in humid environments.	2008-05-15	18546717
Novel multicomponent reactions involving isoquinoline or phenanthridine and activated acetylenic ester in the presence of heterocyclic NH or 1,3-dicarbonyl compounds.	2008-05	18636339
Biotransformation of indole derivatives by mycelial cultures.	2008-04-05	18386493
Semiochemicals of the Scarabaeinae VIII. Identification of active constituents of the abdominal sex-attracting secretion of the male dung beetle, Kheper bonellii, using gas chromatography with flame ionization and electroantennographic detection in parallel.	2008-04-04	17920608
Dual negative precursor ion scan approach for rapid detection of glutathione conjugates using liquid chromatography/tandem mass spectrometry.	2008-04	18320543
Volatile components of Discaria americana Gillies & Hook (Rhamnaceae).	2008-02-15	18266156
Performance of generalist and specialist herbivores and their endoparasitoids differs on cultivated and wild Brassica populations.	2008-02	18231835
Metabolic activation of a novel 3-substituted indole-containing TNF-alpha inhibitor: dehydrogenation and inactivation of CYP3A4.	2008-02	18095656
ESP and ESM1 mediate indol-3-acetonitrile production from indol-3-ylmethyl glucosinolate in Arabidopsis.	2008-02	17920088
Synthesis and evaluation of 3-aryloxymethyl-1,2-dimethylindole-4,7-diones as mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1) activity.	2007-11-15	17944451
Sensory-directed identification of creaminess-enhancing volatiles and semivolatiles in full-fat cream.	2007-11-14	17935296
Gene expression profiles in testis of pigs with extreme high and low levels of androstenone.	2007-11-07	17988377
Detection and structural characterization of glutathione-trapped reactive metabolites using liquid chromatography-high-resolution mass spectrometry and mass defect filtering.	2007-11-01	17918967
Dehydrogenation of indoline by cytochrome P450 enzymes: a novel "aromatase" process.	2007-08	17502430
The role of hydrophobic interactions in positioning of peripheral proteins in membranes.	2007-06-29	17603894
Development of indolequinone mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1): NQO1 inhibition and growth inhibitory activity in human pancreatic MIA PaCa-2 cancer cells.	2007-05-22	17455910
Calculation of the free energy and cooperativity of protein folding.	2007-05-16	17505540
[Identification of volatile organic compounds in the manures of cow, hog and chicken by solid phase microextraction coupled with gas chromatography/mass spectrometry].	2007-05	17679445
Characterization of skatole-producing microbial populations in enriched swine lagoon slurry.	2007-05	17374129
Actions between neonicotinoids and key residues of insect nAChR based on an ab initio quantum chemistry study: hydrogen bonding and cooperative pi-pi interaction.	2007-04-01	17300943
[Exploratory activity of mice of different genetic strains after olfaction disruption by 3-methylindole (skatole)].	2007-03-14	17352200
Olfactory performance of rats after selective deafferentation of the olfactory bulb by 3-methyl indole.	2007-02	17151135
Metabolism and bioactivation of 3-methylindole by human liver microsomes.	2007-01	17226936
Structure and reactivity of Trypanosoma brucei pteridine reductase: inhibition by the archetypal antifolate methotrexate.	2006-09	16968221
Bias of Tedlar bags in the measurement of agricultural odorants.	2006-08-11	16899738
Effect of dietary melengestrol acetate on the incidence of acute interstitial pneumonia in feedlot heifers.	2006-07	16850945
Enzymatic properties of human CYP2W1 expressed in Escherichia coli.	2006-06-23	16677611
Fragmentation of peptides with N-terminal dimethylation and imine/methylol adduction at the tryptophan side-chain.	2006-06	16616858
The role of CYP2A and CYP2E1 in the metabolism of 3-methylindole in primary cultured porcine hepatocytes.	2006-05	16501006
Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells.	2006-03	16544949
CYP4B1: an enigmatic P450 at the interface between xenobiotic and endobiotic metabolism.	2006	16877261
Importance of tensor asymmetry for the analysis of 2H NMR spectra from deuterated aromatic rings.	2005-12-14	16332101
Indole ring oxidation by activated leukocytes prevents the production of hypochlorous acid.	2005-11	16258625
Zafirlukast metabolism by cytochrome P450 3A4 produces an electrophilic alpha,beta-unsaturated iminium species that results in the selective mechanism-based inactivation of the enzyme.	2005-09	16167835
Role of the fermentation process in off-odorant formation in white pepper: on-site trial in Thailand.	2005-07-27	16028995
Characterization of odorants causing an atypical aroma in white pepper powder (Piper nigrum L.) based on quantitative measurements and orthonasal breakthrough thresholds.	2005-07-27	16028994
Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles.	2005-05-16	15848767
Photoreaction between benzoylthiophenes and N-BOC-tryptophan methyl ester.	2005-05-05	15869328

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

10 or 100 uM skatole increased CYP1A1 mRNA expression in HepG2-C3 cells

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:05:10 GMT 2025` Edited by `admin` on `Mon Mar 31 18:05:10 GMT 2025`
Record UNII	9W945B5H7R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SKATOLE

Systematic Name

English

SKATOLUM

Preferred Name

English

SKATOLE [MI]

Common Name

English

3-METHYL-INDOLE

Systematic Name

English

FEMA NO. 3019

Code

English

3-METHYL-1H-INDOLE

Systematic Name

English

SKATOLUM [HPUS]

Common Name

English

SKATOLE [FHFI]

Common Name

English

NSC-122024

Code

English

3-METHYLINDOLE [HSDB]

Common Name

English

Classification Tree Code System Code

JECFA EVALUATION

SKATOLE