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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-22 21:17:53 UTC
HMDB IDHMDB0001527
Secondary Accession Numbers
  • HMDB01527
Metabolite Identification
Common Name3-Methylthiopropionic acid
Description3-Methylthiopropionic acid, also known as 3-(methylsulfanyl)propanoate or 3-methylthiopropanoate, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. 3-Methylthiopropionic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1592860673
Synonyms
ValueSource
3-Methylthiopropanoic acidChEBI
3-(Methylthio)propionic acidKegg
3-MethylthiopropionateKegg
3-(Methylsulfanyl)propanoateKegg
3-MethylthiopropanoateGenerator
3-(Methylthio)propionateGenerator
3-(Methylsulfanyl)propanoic acidGenerator
3-(Methylsulphanyl)propanoateGenerator
3-(Methylsulphanyl)propanoic acidGenerator
4-ThiapentanoateHMDB
4-Thiapentanoic acidHMDB
3-MethylmercaptopropionateHMDB
3-Methylthiopropionate sodium saltHMDB
3-Methyl-thiopropionateHMDB
3-Methylthiopropionic acidGenerator
Chemical FormulaC4H8O2S
Average Molecular Weight120.17
Monoisotopic Molecular Weight120.02450019
IUPAC Name3-(methylsulfanyl)propanoic acid
Traditional Name3-methylthiopropionic acid
CAS Registry Number646-01-5
SMILES
CSCCC(O)=O
InChI Identifier
InChI=1S/C4H8O2S/c1-7-3-2-4(5)6/h2-3H2,1H3,(H,5,6)
InChI KeyCAOMCZAIALVUPA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative Parents
Substituents
  • Straight chain fatty acid
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility28.1 g/LALOGPS
logP0.19ALOGPS
logP0.83ChemAxon
logS-0.63ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.72 m³·mol⁻¹ChemAxon
Polarizability12.22 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006w-9100000000-3cfcc386869df1bf9eadSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9300000000-325fad52ddab47e35b3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-3900000000-4e55d1b8f9820c0c8aa6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9400000000-009a67c09a7b0ea1e6e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-e5e33a00d9d70ebd558aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9100000000-6b3eaab7ae6d34eeb6a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-81e7994d19757c067fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-2100e1cf3bf5bf7a5a2dSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0.036 +/- 0.009 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified0.097 +/- 0.022 umol/mmol creatinineAdult (>18 years old)BothLiver Cirrhosis details
Associated Disorders and Diseases
Disease References
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 ]
Cirrhosis
  1. Yoshida Y: [Analysis of methionine metabolism studied by the gas chromatographic determination of 3-methylthiopropionate in urine and its clinical application]. Hokkaido Igaku Zasshi. 1985 Mar;60(2):183-94. [PubMed:3997054 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022672
KNApSAcK IDC00001194
Chemspider ID547
KEGG Compound IDC08276
BioCyc IDCPD-7672
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6300
PubChem Compound563
PDB IDNot Available
ChEBI ID1438
Food Biomarker OntologyNot Available
VMH IDC08276
References
Synthesis ReferenceWhitehead, Ian M.; Ohleyer, Eric. Process for the production of carboxylic acids from alcohols using Saccharomyces. U.S. (1997), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yoshida Y: [Analysis of methionine metabolism studied by the gas chromatographic determination of 3-methylthiopropionate in urine and its clinical application]. Hokkaido Igaku Zasshi. 1985 Mar;60(2):183-94. [PubMed:3997054 ]
  2. Kaji H, Niioka T, Kojima Y, Yoshida Y, Kawakami Y: Urinary 3-methylthiopropionate excretion and the effect of D- or L-methionine ingestion studied in healthy subjects. Res Commun Chem Pathol Pharmacol. 1987 Apr;56(1):101-9. [PubMed:3589145 ]

Enzymes

General function:
Involved in metal ion binding
Specific function:
Catalyzes the formation of formate and 2-keto-4-methylthiobutyrate (KMTB) from 1,2-dihydroxy-3-keto-5-methylthiopentene (DHK-MTPene). Also down-regulates cell migration mediated by MMP14. Necessary for hepatitis C virus replication in an otherwise non-permissive cell line.
Gene Name:
ADI1
Uniprot ID:
Q9BV57
Molecular weight:
21498.23
Reactions
1,2-Dihydroxy-3-keto-5-methylthiopentene + Oxygen → 3-Methylthiopropionic acid + Formic acid + Carbon monoxidedetails