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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:19:47 UTC
Update Date2019-07-23 05:57:26 UTC
HMDB IDHMDB0012134
Secondary Accession Numbers
  • HMDB12134
Metabolite Identification
Common Name1,2-Dihydroxy-3-keto-5-methylthiopentene
Description1,2-Dihydroxy-3-keto-5-methylthiopentene, also known as 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one or acireductone, belongs to the class of organic compounds known as alpha-branched alpha,beta-unsaturated ketones. These are alpha,beta-unsaturated ketones that carry a branch on the alpha carbon. They have the generic structure RC(=O)C(R')=C, R = organyl group and R'= any heteroatom. 1,2-Dihydroxy-3-keto-5-methylthiopentene is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,2-Dihydroxy-3-keto-5-methylthiopentene exists in all living species, ranging from bacteria to humans. Outside of the human body, 1,2-Dihydroxy-3-keto-5-methylthiopentene has been detected, but not quantified in, several different foods, such as common mushrooms, garden onions, pili nuts, common persimmons, and potato. This could make 1,2-dihydroxy-3-keto-5-methylthiopentene a potential biomarker for the consumption of these foods.
Structure
Data?1563861446
Synonyms
ValueSource
1,2-Dihydroxy-5-(methylsulfanyl)pent-1-en-3-oneChEBI
1,2-Dihydroxy-5-(methylsulphanyl)pent-1-en-3-oneGenerator
AcireductoneHMDB
1,2-Dihydroxy-3-keto-5-methylthiopentaneHMDB
1,2-Dihydroxy-3-keto-5-methylthiopentene anionHMDB
1,2-Dihydroxy-5-(methylthio)pent-1-en-3-oneHMDB
Chemical FormulaC6H10O3S
Average Molecular Weight162.207
Monoisotopic Molecular Weight162.035064876
IUPAC Name(1Z)-1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one
Traditional Name(1Z)-1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one
CAS Registry Number746507-19-7
SMILES
CSCCC(=O)C(\O)=C\O
InChI Identifier
InChI=1S/C6H10O3S/c1-10-3-2-5(8)6(9)4-7/h4,7,9H,2-3H2,1H3/b6-4-
InChI KeyCILXJJLQPTUUSS-XQRVVYSFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-branched alpha,beta-unsaturated ketones. These are alpha,beta-unsaturated ketones that carry a branch on the alpha carbon. They have the generic structure RC(=O)C(R')=C, R = organyl group and R'= any heteroatom.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-branched alpha,beta-unsaturated ketones
Alternative Parents
Substituents
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Vinylogous acid
  • Enone
  • Alpha-hydroxy ketone
  • Acryloyl-group
  • Ketone
  • Enediol
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

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 Solubility8.75 g/LALOGPS
logP0.07ALOGPS
logP0.81ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)8.1ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity41.87 m³·mol⁻¹ChemAxon
Polarizability16.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-9300000000-19a09fc38a4607410081Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-025c-9170000000-6b6fd50d76488524c888Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-523c47d24f3c45c4f285Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07xs-9700000000-cbbc0baabd68adaf65adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-c591ef1f6d20bddce525Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9300000000-bd31c9d726fbcfa6d7e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000000-4d0c04f4b382ef0d5b9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-96c889c8c6acb6410bf6Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030186
KNApSAcK IDNot Available
Chemspider ID4575316
KEGG Compound IDC15606
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5462190
PDB IDNot Available
ChEBI ID49252
Food Biomarker OntologyNot Available
VMH IDM00245
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme that catalyzes the enolization of 2,3-diketo-5-methylthiopentyl-1-phosphate (DK-MTP-1-P) into the intermediate 2-hydroxy-3-keto-5-methylthiopentenyl-1-phosphate (HK-MTPenyl-1-P), which is then dephosphorylated to form the acireductone 1,2-dihydroxy-3-keto-5-methylthiopentene (DHK-MTPene).
Gene Name:
ENOPH1
Uniprot ID:
Q9UHY7
Molecular weight:
28932.44
Reactions
5-(Methylthio)-2,3-dioxopentyl phosphate + Water → 1,2-Dihydroxy-3-keto-5-methylthiopentene + Phosphatedetails
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 → 2-Oxo-4-methylthiobutanoic acid + Formic aciddetails
1,2-Dihydroxy-3-keto-5-methylthiopentene + Oxygen → 3-Methylthiopropionic acid + Formic acid + Carbon monoxidedetails