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Identification
YMDB IDYMDB00185
Name1,2-Dihydroxy-3-keto-5-methylthiopentene
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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. Within yeast, 1,2-dihydroxy-3-keto-5-methylthiopentene participates in a number of enzymatic reactions. In particular, 1,2-dihydroxy-3-keto-5-methylthiopentene can be converted into 2-oxo-4-methylthiobutanoic acid and formic acid through its interaction with the enzyme acireductone dioxygenase. In addition, 1,2-dihydroxy-3-keto-5-methylthiopentene can be biosynthesized from 5-(methylthio)-2,3-dioxopentyl phosphate; which is mediated by the enzyme 2,3-dioxomethiopentane-1-phosphate enolase/phosphatase. In yeast, 1,2-dihydroxy-3-keto-5-methylthiopentene is involved in the metabolic pathway called the methionine metabolism and salvage pathway.
Structure
Thumb
Synonyms
  • 1,2-dihydroxy-3-keto-5-methylthiopentane
  • 1,2-dihydroxy-3-keto-5-methylthiopentene anion
  • 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one
  • 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one
  • 1,2-Dihydroxy-5-(methylsulphanyl)pent-1-en-3-one
  • Acireductone
CAS number746507-19-7
WeightAverage: 162.207
Monoisotopic: 162.035064876
InChI KeyCILXJJLQPTUUSS-XQRVVYSFSA-N
InChIInChI=1S/C6H10O3S/c1-10-3-2-5(8)6(9)4-7/h4,7,9H,2-3H2,1H3/b6-4-
IUPAC Name(1Z)-1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one
Traditional IUPAC Name(1Z)-1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one
Chemical FormulaC6H10O3S
SMILES[H]OC([H])=C(O[H])C(=O)C([H])([H])C([H])([H])SC([H])([H])[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Nucleus
Organoleptic PropertiesNot Available
SMPDB Pathways
Methionine metabolism and salvagePW002384 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
SMPDB Reactions
1,2-Dihydroxy-3-keto-5-methylthiopentene + oxygen4-Methylthio-2-oxobutanoate + hydron + Formic acid
water + 5-(methylsulfanyl)-2,3-dioxopentyl phosphate hydron + phosphate + 1,2-Dihydroxy-3-keto-5-methylthiopentene
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID49252
HMDB IDHMDB12134
Pubchem Compound ID5462190
Kegg IDC15606
ChemSpider ID4575316
FOODB IDFDB028796
Wikipedia IDNot Available
BioCyc IDCPD-85

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:
UTR4
Uniprot ID:
P32626
Molecular weight:
25187.19922
Reactions
5-(methylthio)-2,3-dioxopentyl phosphate + H(2)O → 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + phosphate.
2-Phosphoglycolate + H2O → glycolate + phosphate