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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:45:30 UTC
HMDB IDHMDB0001527
Secondary Accession Numbers
  • HMDB01527
Metabolite Identification
Common Name3-Methylthiopropionic acid
Description3-methylthiopropionate is one of the metabolites of methionine (especially of D-methionine) and pharmacokinetics of 3-MTP in urine seems to contribute to the clinicopathological investigation of the liver cirrhosis. (PMID 3997054 ).
Structure
Thumb
Synonyms
ValueSource
3-Methylthiopropanoic acidChEBI
3-MethylthiopropanoateGenerator
3-MethylthiopropionateGenerator
3-(Methylsulfanyl)propanoateHMDB
3-(Methylsulfanyl)propanoic acidHMDB
3-(methylthio)PropionateHMDB
3-(methylthio)Propionic acidHMDB
4-ThiapentanoateHMDB
4-Thiapentanoic acidHMDB
3-MethylmercaptopropionateMeSH
3-Methylthiopropionate sodium saltMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006w-9100000000-3cfcc386869df1bf9eadView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9300000000-325fad52ddab47e35b3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-3900000000-4e55d1b8f9820c0c8aa6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-9400000000-009a67c09a7b0ea1e6e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-e5e33a00d9d70ebd558aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9100000000-6b3eaab7ae6d34eeb6a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-81e7994d19757c067fbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-2100e1cf3bf5bf7a5a2dView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0.036 +/- 0.009 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>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
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 IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022672
KNApSAcK IDNot Available
Chemspider ID547
KEGG Compound IDC08276
BioCyc IDCPD-86
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6300
PubChem Compound563
PDB IDNot Available
ChEBI ID1438
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