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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-07-12 23:01:06 UTC
HMDB IDHMDB0000466
Secondary Accession Numbers
  • HMDB00466
Metabolite Identification
Common Name3-Methylindole
Description3-Methylindole, or skatole, belongs to the indole family and has a methyl substituent in position 3 of the indole ring. It occurs naturally in feces, beets, and coal tar, and has a strong fecal odor. Its name is derived from skato, the Greek word for dung. It exists as a white crystalline or fine powder solid, and it browns upon aging. 3-Methylindole is produced from tryptophan in the mammalian digestive tract where tryptophan is converted to indoleacetic acid, which decarboxylates to give the methylindole. These reactions are largely driven by the microbiota in the digestive tract. 3-Methylindole is soluble in alcohol and benzene and it gives violet color in potassium ferrocyanide (K4Fe(CN)6.3H2O) mixed with sulfuric acid (H2SO4). Skatole has a double ring system which displays aromaticity that comes from the lone pair electrons on the nitrogen. It is continuous (all atoms in the ring are sp2 hybridized), planar, and follows the 4n+2 rule because it has 10 pi electrons. In a 1994 report released by five top cigarette companies, skatole was listed as one of the 599 additives to cigarettes. This is because in low concentrations skatole has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana. As a result, skatole/3-methylindole is used as a fragrance and fixative in many perfumes and as a general aroma compound for other applications. 3-Methylindole has been found to be a bacterial metabolite of members of the Clostridium (PMID: 18223109 ) and Lactobacillus (PMID: 16345702 ) families. Skatole functions as an insect attractant and is one of many compounds that are attractive to males of various species of orchid bees, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait for these bees for study (PMID: 12647866 ). It is also known for being an attractant for the Tasmanian grass grub beetle (Aphodius tasmaniae). Skatole has also been shown to be an attractant to gravid mosquitoes in both field and laboratory conditions (PMID: 24242053 ).
Structure
Data?1582752133
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 Weight131.1745
Monoisotopic Molecular Weight131.073499293
IUPAC Name3-methyl-1H-indole
Traditional Namescatole
CAS Registry Number83-34-1
SMILES
CC1=CNC2=C1C=CC=C2
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
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point97.5 °CNot Available
Boiling Point265.00 to 266.00 °C. @ 755.00 mm HgThe Good Scents Company Information System
Water Solubility0.5 mg/mLNot Available
LogP2.60HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.09 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.16231661259
DarkChem[M-H]-125.87531661259
AllCCS[M+H]+123.60232859911
AllCCS[M-H]-123.85632859911
DeepCCS[M+H]+126.60130932474
DeepCCS[M-H]-123.43730932474
DeepCCS[M-2H]-160.38930932474
DeepCCS[M+Na]+135.43530932474
AllCCS[M+H]+123.632859911
AllCCS[M+H-H2O]+118.632859911
AllCCS[M+NH4]+128.232859911
AllCCS[M+Na]+129.632859911
AllCCS[M-H]-123.932859911
AllCCS[M+Na-2H]-124.932859911
AllCCS[M+HCOO]-126.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-MethylindoleCC1=CNC2=C1C=CC=C22474.7Standard polar33892256
3-MethylindoleCC1=CNC2=C1C=CC=C21372.9Standard non polar33892256
3-MethylindoleCC1=CNC2=C1C=CC=C21386.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methylindole,1TMS,isomer #1CC1=CN([Si](C)(C)C)C2=CC=CC=C121599.7Semi standard non polar33892256
3-Methylindole,1TMS,isomer #1CC1=CN([Si](C)(C)C)C2=CC=CC=C121508.5Standard non polar33892256
3-Methylindole,1TMS,isomer #1CC1=CN([Si](C)(C)C)C2=CC=CC=C121695.4Standard polar33892256
3-Methylindole,1TBDMS,isomer #1CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C121831.2Semi standard non polar33892256
3-Methylindole,1TBDMS,isomer #1CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C121700.0Standard non polar33892256
3-Methylindole,1TBDMS,isomer #1CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C121843.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Methylindole EI-B (Non-derivatized)splash10-0ufr-9200000000-251c9585af60abc11fb12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylindole EI-B (Non-derivatized)splash10-0ufr-9200000000-251c9585af60abc11fb12018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylindole GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1900000000-f9bb0d50c5d49c2c6c4a2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylindole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylindole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-dba6ed7df0e1ee94cafe2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylindole Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0900000000-a7cd474bc90f9a0227e52012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylindole Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014i-2900000000-cb7f6d8c4ad7b0a1523b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylindole Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000l-9200000000-e9a200fb7b8fc93ced482012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylindole EI-B (HITACHI M-80) , Positive-QTOFsplash10-0ufr-9200000000-7120fbb6f78f440ff7252012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylindole Linear Ion Trap , negative-QTOFsplash10-002b-9800000000-a8de490dffcbc2cb0c242017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 10V, Positive-QTOFsplash10-001i-0900000000-355610a12cde08bb25c82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 20V, Positive-QTOFsplash10-001i-0900000000-36a1bcb0093fec9dd5c52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 40V, Positive-QTOFsplash10-0zfr-3900000000-d8aebbf9a6779cddc7352015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 10V, Negative-QTOFsplash10-001i-0900000000-ed646ab44a1fcc84725b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 20V, Negative-QTOFsplash10-001i-0900000000-ed6f0939d3598782a8932015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 40V, Negative-QTOFsplash10-0f89-2900000000-a801a40b2fcba369d3d42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 10V, Negative-QTOFsplash10-001i-0900000000-244a9c7ac26f199509262021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 20V, Negative-QTOFsplash10-001i-0900000000-e7c79bc3a884b9bd7abe2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 40V, Negative-QTOFsplash10-004i-1900000000-e057600f7f225ff9cec22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 10V, Positive-QTOFsplash10-001i-0900000000-f53b130d6fbd7a49b7bd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 20V, Positive-QTOFsplash10-001i-0900000000-92ee6b9af4d8ea4f32d42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylindole 40V, Positive-QTOFsplash10-0v00-7900000000-f01b3fb9a64effb7bb2e2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified12189.869 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified2248.913 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified2975.68 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Bothautism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004302
KNApSAcK IDC00001430
Chemspider ID6480
KEGG Compound IDC08313
BioCyc IDSKATOLE
BiGG IDNot Available
Wikipedia LinkSkatole
METLIN ID5453
PubChem Compound6736
PDB IDNot Available
ChEBI ID9171
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006331
References
Synthesis ReferenceXu, Jianguo; Xu, Lili; Shi, Hongxin. Synthesis of 3-methylindole and its new purification method. Huagong Shengchan Yu Jishu (2005), 12(4), 12-14.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Karlin DA, Mastromarino AJ, Jones RD, Stroehlein JR, Lorentz O: Fecal skatole and indole and breath methane and hydrogen in patients with large bowel polyps or cancer. J Cancer Res Clin Oncol. 1985;109(2):135-41. [PubMed:3980562 ]
  2. Moore JG, Jessop LD, Osborne DN: Gas-chromatographic and mass-spectrometric analysis of the odor of human feces. Gastroenterology. 1987 Dec;93(6):1321-9. [PubMed:3678751 ]
  3. Cooke M, Leeves N, White C: Time profile of putrescine, cadaverine, indole and skatole in human saliva. Arch Oral Biol. 2003 Apr;48(4):323-7. [PubMed:12663078 ]
  4. Zuccato E, Venturi M, Di Leo G, Colombo L, Bertolo C, Doldi SB, Mussini E: Role of bile acids and metabolic activity of colonic bacteria in increased risk of colon cancer after cholecystectomy. Dig Dis Sci. 1993 Mar;38(3):514-9. [PubMed:8444084 ]
  5. Muller T, Thissen R, Braun S, Dott W, Fischer G: (M)VOC and composting facilities. Part 2: (M)VOC dispersal in the environment. Environ Sci Pollut Res Int. 2004;11(3):152-7. [PubMed:15259697 ]
  6. Codipilly DP, Kaufman HW, Kleinberg I: Use of a novel group of oral malodor measurements to evaluate an anti-oral malodor mouthrinse (TriOralTM) in humans. J Clin Dent. 2004;15(4):98-104. [PubMed:15794454 ]
  7. 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 ]
  8. Yokoyama MT, Carlson JR: Production of Skatole and para-Cresol by a Rumen Lactobacillus sp. Appl Environ Microbiol. 1981 Jan;41(1):71-6. [PubMed:16345702 ]

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:
CYP2F1
Uniprot ID:
P24903
Molecular weight:
55500.64
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