Showing Compound Card for Skatole (CDB005371)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 1 proteinXML
Record Information
Version1.0
Created at2020-04-27 16:13:56 UTC
Updated at2021-01-04 20:37:41 UTC
CannabisDB IDCDB005371
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameSkatole
Description3-Methylindole,  C9H9N, or skatole, belongs to the indole family and has a methyl substituent in position 3 of the indole ring. Its name is derived from skato, the Greek word for dung. 3-Methylindole is a mildly toxic, white crystalline solid that browns upon aging and is insoluble in water. It is soluble in alcohol and benzene and has a strong fecal odor. It reacts with potassium ferrocyanide (K4Fe(CN)6.3H2O) and sulfuric acid (H2SO4) to give a violet color. It can be made through Fischer indole synthesis which was developed by Emil Fischer. It occurs naturally in feces as it is produced by microbial degradation of tryptophan in the mammalian digestive tract (¬†PMID:¬†367144). It is also found in tea leaf, coffee, milk, butter, beets, beet root, rice bran, squid, pork, mozzarella and swiss cheese and coal tar ( Ref:DOI ). In low concentrations it has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana. It is used as a fragrance and fixative in many perfumes and as an aroma compound as well as a flavoring ingredient. In a 1994 report released by five top cigarette companies, skatole was listed as one of the 599 additives to cigarettes. 3-Methylindole is a metabolite of Clostridium (PMID: 18223109 ) and Lactobacillus (PMID: 16345702 ). It is an insect attractant for orchid bees (PMID:¬†12647866), grub beetles ( Ref:DOI ) and gravid mosquitoes (¬†PMID:¬†24242053). It also may be a toxin as it causes transient olfactory mucosal injury in ponies (PMID:¬†26486918). 3-Methylindole is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-Methyl-4,5-benzopyrroleChEBI
beta-MethylindoleChEBI
SkatolChEBI
b-MethylindoleGenerator
Β-methylindoleGenerator
3-Methyl-1H-indoleHMDB
3-MIHMDB
ScatoleHMDB
SkatoleHMDB
3 MethylindoleHMDB
3-MethylindoleChEBI
Chemical FormulaC9H9N
Average Molecular Weight131.17
Monoisotopic Molecular Weight131.0735
IUPAC Name3-methyl-1H-indole
Traditional Namescatole
CAS Registry Number83-34-1
SMILES
CC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3
InChI KeyZFRKQXVRDFCRJG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-methylindoles. These are aromatic heterocyclic compounds that contain an indole moiety substituted at the 3-position with a methyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-methylindoles
Alternative Parents
Substituents
  • 3-methylindole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point97.5 °CNot Available
Boiling Point265 °CWikipedia
Water Solubility0.5 mg/mLNot Available
logP2.60HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP2.58ALOGPS
logP2.59ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)17.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.19 m³·mol⁻¹ChemAxon
Polarizability14.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-dba6ed7df0e1ee94cafe2015-03-01View Spectrum
GC-MSSkatole, non-derivatized, GC-MS Spectrumsplash10-0ufr-9200000000-251c9585af60abc11fb1Spectrum
GC-MSSkatole, non-derivatized, GC-MS Spectrumsplash10-0ufr-9200000000-251c9585af60abc11fb1Spectrum
Predicted GC-MSSkatole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-1900000000-f9bb0d50c5d49c2c6c4aSpectrum
Predicted GC-MSSkatole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSkatole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-a7cd474bc90f9a0227e52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-2900000000-cb7f6d8c4ad7b0a1523b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000l-9200000000-e9a200fb7b8fc93ced482012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0ufr-9200000000-7120fbb6f78f440ff7252012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-002b-9800000000-a8de490dffcbc2cb0c242017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-355610a12cde08bb25c82015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-36a1bcb0093fec9dd5c52015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-3900000000-d8aebbf9a6779cddc7352015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-ed646ab44a1fcc84725b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-ed6f0939d3598782a8932015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f89-2900000000-a801a40b2fcba369d3d42015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-244a9c7ac26f199509262021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-e7c79bc3a884b9bd7abe2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-e057600f7f225ff9cec22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-f53b130d6fbd7a49b7bd2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-92ee6b9af4d8ea4f32d42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-7900000000-f01b3fb9a64effb7bb2e2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cytochrome P450 2F1CYP2F119q13.2P24903 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000466
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004302
KNApSAcK IDC00001430
Chemspider ID6480
KEGG Compound IDC08313
BioCyc IDSKATOLE
BiGG IDNot Available
Wikipedia LinkSkatole
METLIN ID5453
PubChem Compound6736
PDB IDNot Available
ChEBI ID9171
References
General References
  1. Whitehead TR, Price NP, Drake HL, Cotta MA: Catabolic pathway for the production of skatole and indoleacetic acid by the acetogen Clostridium drakei, Clostridium scatologenes, and swine manure. Appl Environ Microbiol. 2008 Mar;74(6):1950-3. doi: 10.1128/AEM.02458-07. Epub 2008 Jan 25. [PubMed:18223109 ]
  2. Yokoyama MT, Carlson JR: Production of Skatole and para-Cresol by a Rumen Lactobacillus sp. Appl Environ Microbiol. 1981 Jan;41(1):71-6. doi: 10.1128/AEM.41.1.71-76.1981. [PubMed:16345702 ]