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Record Information
Version3.6
Creation Date2006-05-22 15:12:42 UTC
Update Date2016-02-11 01:06:07 UTC
HMDB IDHMDB03227
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethanethiol
DescriptionMethanethiol (also known as methyl mercaptan) is a colorless gas that smells like rotten cabbage. It is a natural substance found in the blood, brain, and other tissues of people and animals. It is released from animal feces. It occurs naturally in certain foods, such as some nuts and cheese. It is also one of the main chemicals responsible for bad breath and flatulence. At very high concentrations methanethiol is highly toxic and affects the central nervous system. The chemical formula for methanethiol is CH3SH; it is classified as a thiol. Methanethiol is also considered to be a weak acid, with a pKa of ~10.4. This acidic property makes it reactive with dissolved metals in aqueous solutions. The environmental chemistry of these interactions in seawater or fresh water environments such as lakes has yet to be fully investigated. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
MethylmercaptanChEBI
CH3SHHMDB
Mercaptan methyliqueHMDB
MercaptomethaneHMDB
MethanethioleHMDB
MethanthiolHMDB
MethvtioloHMDB
Methyl mercaptanHMDB
Methyl sulfhydrateHMDB
Methyl thioalcoholHMDB
MethylmercaptaanHMDB
MetilmercaptanoHMDB
ThiomethaneHMDB
ThiomethanolHMDB
Chemical FormulaCH4S
Average Molecular Weight48.107
Monoisotopic Molecular Weight48.003370818
IUPAC Namemethanethiol
Traditional Namemethanethiol
CAS Registry Number74-93-1
SMILES
CS
InChI Identifier
InChI=1S/CH4S/c1-2/h2H,1H3
InChI KeyInChIKey=LSDPWZHWYPCBBB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiols
Sub ClassAlkylthiols
Direct ParentAlkylthiols
Alternative Parents
Substituents
  • Alkylthiol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Osmolyte, enzyme cofactor, signalling
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateGas
Experimental Properties
PropertyValueReference
Melting Point-123 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility15.4 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility20.0 mg/mLALOGPS
logP0.73ALOGPS
logP0.84ChemAxon
logS-0.38ALOGPS
pKa (Strongest Acidic)10.34ChemAxon
pKa (Strongest Basic)-9.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.24 m3·mol-1ChemAxon
Polarizability5.33 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-d6688241d1bd9d04eb37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-d6688241d1bd9d04eb37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-d6688241d1bd9d04eb37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-56912dcbda83e96bbb38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-56912dcbda83e96bbb38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-56912dcbda83e96bbb38View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-53d9f1ccbdb100d7320dView in MoNA
1D NMR1H NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • colon
  • Fibroblasts
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.7 +/- 0.3 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.516 +/- 0.068 uMAdult (>18 years old)BothCirrhosis details
BloodDetected and Quantified1.211 +/- 0.128 uMAdult (>18 years old)Both
Cirrhosis
details
BloodDetected and Quantified7.7 +/- 1.1 uMAdult (>18 years old)BothLiver disease (non-encephalopathic) details
BloodDetected and Quantified13.2 +/- 1.0 uMAdult (>18 years old)BothLiver disease (encephalopathic) details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. McClain CJ, Zieve L, Doizaki WM, Gilberstadt S, Onstad GR: Blood methanethiol in alcoholic liver disease with and without hepatic encephalopathy. Gut. 1980 Apr;21(4):318-23. [7429293 ]
Liver disease
  1. Fabbri EL, Hamner LH 3rd: Congenital complete heart block associated with maternal anti-Ro antibody: a case report. J Perinatol. 1992 Sep;12(3):225-8. [1432277 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011886
KNApSAcK IDC00001258
Chemspider ID855
KEGG Compound IDC00409
BioCyc IDMETHANETHIOL
BiGG IDNot Available
Wikipedia LinkMethanethiol
NuGOwiki LinkHMDB03227
Metagene LinkHMDB03227
METLIN ID3204
PubChem Compound878
PDB IDMEE
ChEBI ID16007
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jiang T, Suarez FL, Levitt MD, Nelson SE, Ziegler EE: Gas production by feces of infants. J Pediatr Gastroenterol Nutr. 2001 May;32(5):534-41. [11429513 ]
  2. Walker V, Mills GA, Fortune PM, Wheeler R: Neonatal encephalopathy with a pungent body odour. Arch Dis Child Fetal Neonatal Ed. 1997 Jul;77(1):F65-6. [9279187 ]
  3. Suarez F, Springfield J, Furne J, Levitt M: Differentiation of mouth versus gut as site of origin of odoriferous breath gases after garlic ingestion. Am J Physiol. 1999 Feb;276(2 Pt 1):G425-30. [9950816 ]
  4. Yaegaki K, Sanada K: Volatile sulfur compounds in mouth air from clinically healthy subjects and patients with periodontal disease. J Periodontal Res. 1992 Jul;27(4 Pt 1):233-8. [1640345 ]
  5. Suarez FL, Furne J, Springfield J, Levitt MD: Failure of activated charcoal to reduce the release of gases produced by the colonic flora. Am J Gastroenterol. 1999 Jan;94(1):208-12. [9934757 ]
  6. Jonski G, Young A, Waler SM, Rolla G: Insoluble zinc, cupric and tin pyrophosphates inhibit the formation of volatile sulphur compounds. Eur J Oral Sci. 2004 Oct;112(5):429-32. [15458502 ]
  7. Hayward NJ, Jeavons TH, Nicholson AJ, Thornton AG: Development of specific tests for rapid detection of Escherichia coli and all species of Proteus in urine. J Clin Microbiol. 1977 Sep;6(3):195-201. [332706 ]
  8. Johnson PW, Lancero H: Function of gingival fibroblasts and periodontal ligament cells in the presence of methyl mercaptan. Quintessence Int. 1999 May;30(5):343-9. [10635290 ]