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1,2-Dihydroxy-3-keto-5-methylthiopentene (YMDB00185)

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, 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 exists in all living species, ranging from bacteria to plants to humans. In yeast, 1,2-dihydroxy-3-keto-5-methylthiopentene is involved in the metabolic pathway called the methionine metabolism and salvage pathway. Based on a literature review a small amount of articles have been published on 1,2-Dihydroxy-3-keto-5-methylthiopentene.
Structure
Thumb
MOLSDFPDBSMILESInChI
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)8.31ChemAxon
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 + oxygen → 4-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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-9300000000-19a09fc38a4607410081JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-025c-9170000000-6b6fd50d76488524c888JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-523c47d24f3c45c4f285JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07xs-9700000000-cbbc0baabd68adaf65adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-c591ef1f6d20bddce525JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9300000000-bd31c9d726fbcfa6d7e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000000-4d0c04f4b382ef0d5b9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-96c889c8c6acb6410bf6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ik9-7900000000-4e7dffabd3e521b59a33JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bta-9000000000-4dee6c63f979437272b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-9000000000-e4050047631669464d94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9100000000-6f5f734e698f1dbf5d5cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-e1d92d2a30bee517d754JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-e1d92d2a30bee517d754JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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

Protein Details
1. Enolase-phosphatase E1
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