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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 of SKATOLE

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
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

Brieger, L.
1
Curator's Comment: Skatole was discovered in 1877 by the German physician Ludwig Brieger

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Partial Agonist
290
Inhibitor
8297
 0.024 mM [EC50]
cytochrome P450 2A19
2
Target ID: 403149.0
Gene Symbol: CYP2A19
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Importance of tensor asymmetry for the analysis of 2H NMR spectra from deuterated aromatic rings.
2005 Dec 14
Role of the fermentation process in off-odorant formation in white pepper: on-site trial in Thailand.
2005 Jul 27
Characterization of odorants causing an atypical aroma in white pepper powder (Piper nigrum L.) based on quantitative measurements and orthonasal breakthrough thresholds.
2005 Jul 27
Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles.
2005 May 16
Indole ring oxidation by activated leukocytes prevents the production of hypochlorous acid.
2005 Nov
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 Sep
CYP4B1: an enigmatic P450 at the interface between xenobiotic and endobiotic metabolism.
2006
Photoreaction between benzoylthiophenes and N-BOC-tryptophan methyl ester.
2006 Jan-Feb
Effect of dietary melengestrol acetate on the incidence of acute interstitial pneumonia in feedlot heifers.
2006 Jul
Fragmentation of peptides with N-terminal dimethylation and imine/methylol adduction at the tryptophan side-chain.
2006 Jun
Enzymatic properties of human CYP2W1 expressed in Escherichia coli.
2006 Jun 23
Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells.
2006 Mar
The role of CYP2A and CYP2E1 in the metabolism of 3-methylindole in primary cultured porcine hepatocytes.
2006 May
Structure and reactivity of Trypanosoma brucei pteridine reductase: inhibition by the archetypal antifolate methotrexate.
2006 Sep
Bias of Tedlar bags in the measurement of agricultural odorants.
2006 Sep-Oct
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 Apr 1
Dehydrogenation of indoline by cytochrome P450 enzymes: a novel "aromatase" process.
2007 Aug
Olfactory performance of rats after selective deafferentation of the olfactory bulb by 3-methyl indole.
2007 Feb
Metabolism and bioactivation of 3-methylindole by human liver microsomes.
2007 Jan
[Exploratory activity of mice of different genetic strains after olfaction disruption by 3-methylindole (skatole)].
2007 Jan-Feb
The role of hydrophobic interactions in positioning of peripheral proteins in membranes.
2007 Jun 29
[Identification of volatile organic compounds in the manures of cow, hog and chicken by solid phase microextraction coupled with gas chromatography/mass spectrometry].
2007 May
Characterization of skatole-producing microbial populations in enriched swine lagoon slurry.
2007 May
Calculation of the free energy and cooperativity of protein folding.
2007 May 16
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 May 22
Detection and structural characterization of glutathione-trapped reactive metabolites using liquid chromatography-high-resolution mass spectrometry and mass defect filtering.
2007 Nov 1
Sensory-directed identification of creaminess-enhancing volatiles and semivolatiles in full-fat cream.
2007 Nov 14
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 Nov 15
Gene expression profiles in testis of pigs with extreme high and low levels of androstenone.
2007 Nov 7
Dual negative precursor ion scan approach for rapid detection of glutathione conjugates using liquid chromatography/tandem mass spectrometry.
2008 Apr
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 Apr 4
Reverse and conventional chemical ecology approaches for the development of oviposition attractants for Culex mosquitoes.
2008 Aug 22
Gene expression profiles in liver of pigs with extreme high and low levels of androstenone.
2008 Aug 6
The chromatin remodeler SPLAYED regulates specific stress signaling pathways.
2008 Dec
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 Dec 11
Performance of generalist and specialist herbivores and their endoparasitoids differs on cultivated and wild Brassica populations.
2008 Feb
Metabolic activation of a novel 3-substituted indole-containing TNF-alpha inhibitor: dehydrogenation and inactivation of CYP3A4.
2008 Feb
ESP and ESM1 mediate indol-3-acetonitrile production from indol-3-ylmethyl glucosinolate in Arabidopsis.
2008 Feb
Volatile components of Discaria americana Gillies & Hook (Rhamnaceae).
2008 Feb 15
Biotransformation of indole derivatives by mycelial cultures.
2008 Jan-Feb
Novel multicomponent reactions involving isoquinoline or phenanthridine and activated acetylenic ester in the presence of heterocyclic NH or 1,3-dicarbonyl compounds.
2008 May
Field sampling method for quantifying odorants in humid environments.
2008 May 15
L-tryptophan radical cation electron spin resonance studies: connecting solution-derived hyperfine coupling constants with protein spectral interpretations.
2008 May 21
Effect of ginkgo biloba and dexamethasone in the treatment of 3-methylindole-induced anosmia mouse model.
2008 May-Jun
Carbohydrate-protein recognition probed by density functional theory and ab initio calculations including dispersive interactions.
2008 Nov 21
Mechanism of the efficient tryptophan fluorescence quenching in human gammaD-crystallin studied by time-resolved fluorescence.
2008 Oct 7
Single mutations change CYP2F3 from a dehydrogenase of 3-methylindole to an oxygenase.
2008 Sep 16
Fe(III) stimulates 3-methylindole and 4-methylphenol production in swine lagoon enrichments and Clostridium scatologenes ATCC 25775.
2009 Jan
3-Methylindole production is regulated in Clostridium scatologenes ATCC 25775.
2009 Jan
Solvent effects on the fluorescence quenching of tryptophan by amides via electron transfer. Experimental and computational studies.
2009 Mar 5
Patents

Patents

04436746
1
05907045
1
06297387
1
06448243
13
06579881
13
07569604
1
07709466
3
07968546
3
08173646
4
08586546
7
08835689
1
JP2000210526A
1
JP2003125919A
1
JP2006311924A
4
JP2007534619A
2
JP2008523082A
1
JP2009523713A
1
JPH02240072A
7
JPH0253482A
1
JPH05178891A
1
JPH06206805A
1
JPH11335218A
1
JPS579719A
1
JPS61162751A
1
JPS6261958A
1
JPS6431728A
1

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 Fri Dec 15 15:40:41 UTC 2023
Edited
by admin
on Fri Dec 15 15:40:41 UTC 2023
Record UNII
9W945B5H7R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SKATOLE
FHFI   MI  
Systematic 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
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
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
NCI_THESAURUS C45564
Created by admin on Fri Dec 15 15:40:42 UTC 2023 , Edited by admin on Fri Dec 15 15:40:42 UTC 2023
Code System Code Type Description
JECFA MONOGRAPH
1188
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
PRIMARY
NCI_THESAURUS
C87586
Created by admin on Fri Dec 15 15:40:42 UTC 2023 , Edited by admin on Fri Dec 15 15:40:42 UTC 2023
PRIMARY
CAS
83-34-1
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
PRIMARY
PUBCHEM
6736
Created by admin on Fri Dec 15 15:40:42 UTC 2023 , Edited by admin on Fri Dec 15 15:40:42 UTC 2023
PRIMARY
CHEBI
9171
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
PRIMARY
NSC
122024
Created by admin on Fri Dec 15 15:40:42 UTC 2023 , Edited by admin on Fri Dec 15 15:40:42 UTC 2023
PRIMARY
FDA UNII
9W945B5H7R
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID8021775
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
PRIMARY
HSDB
3511
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
PRIMARY
MERCK INDEX
m9968
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
SKATOLE
Created by admin on Fri Dec 15 15:40:42 UTC 2023 , Edited by admin on Fri Dec 15 15:40:42 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-471-7
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
PRIMARY
MESH
D012862
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
PRIMARY
DAILYMED
9W945B5H7R
Created by admin on Fri Dec 15 15:40:41 UTC 2023 , Edited by admin on Fri Dec 15 15:40:41 UTC 2023
PRIMARY
RXCUI
1311386
Created by admin on Fri Dec 15 15:40:42 UTC 2023 , Edited by admin on Fri Dec 15 15:40:42 UTC 2023
PRIMARY RxNorm
Related Record Type Details
Structure of 3-METHYL-2-INDOLINONE
METABOLITE -> PARENT
IN-VITRO
Scientific Literature
Related Record Type Details
Structure of SKATOLE
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