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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2019-07-23 07:12:36 UTC
HMDB IDHMDB0059620
Secondary Accession Numbers
  • HMDB0060266
  • HMDB0062750
  • HMDB59620
  • HMDB60266
  • HMDB62750
Metabolite Identification
Common Name5-(Methylthio)-2,3-dioxopentyl phosphate
Description5-(Methylthio)-2,3-dioxopentyl phosphate, also known as 1-phospho-2,3-diketo-5-S-methylthiopentane or 2,3-diketo-5-methylthiopentyl-1-phosphate (DK-MTP-1-P), belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. 5-(Methylthio)-2,3-dioxopentyl phosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 5-(Methylthio)-2,3-dioxopentyl phosphate exists in all eukaryotes, ranging from yeast to humans. 5-(Methylthio)-2,3-dioxopentyl phosphate is a metabolite involved in the cysteine and methionine metabolism pathway. It is a substrate for both E1 enolase-phosphatase and methylthioribulose-1-phosphate dehydratase. Outside of the human body, 5-(methylthio)-2,3-dioxopentyl phosphate can be found in a number of food items such as lime, pineapple, spearmint, and yautia. This makes 5-(methylthio)-2,3-dioxopentyl phosphate a potential biomarker for the consumption of these food products.
Structure
Data?1563865956
Synonyms
ValueSource
1-Phospho-2,3-diketo-5-S-methylthiopentaneChEBI
2,3-Diketo-5-methylthio-1-phosphopentaneChEBI
2,3-Diketo-5-methylthiopentyl-1-phosphateChEBI
5-Methylthio-1-(phosphonooxy)pentane-2,3-dioneChEBI
2,3-Diketo-5-methylthiopentyl-1-phosphoric acidGenerator
5-(Methylthio)-2,3-dioxopentyl phosphoric acidGenerator
1-PDMSPMeSH
5-(Methylthio)-2,3-dioxopentyl phosphateChEBI
5-(Methylthio)-1-(phosphonooxy)-2,3-pentanedioneHMDB
5-(Methylsulfanyl)-2,3-dioxopentyl phosphateHMDB
DK-MTP-1-PHMDB
Chemical FormulaC6H11O6PS
Average Molecular Weight242.187
Monoisotopic Molecular Weight242.001395286
IUPAC Name{[5-(methylsulfanyl)-2,3-dioxopentyl]oxy}phosphonic acid
Traditional Name1-pdmsp
CAS Registry Number115974-73-7
SMILES
CSCCC(=O)C(=O)COP(O)(O)=O
InChI Identifier
InChI=1S/C6H11O6PS/c1-14-3-2-5(7)6(8)4-12-13(9,10)11/h2-4H2,1H3,(H2,9,10,11)
InChI KeyHKEAOVFNWRDVAJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Monosaccharide
  • Alpha-diketone
  • Ketone
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
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 Solubility7.99 g/LALOGPS
logP-0.08ALOGPS
logP0.51ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.11ChemAxon
pKa (Strongest Basic)-9.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity51.2 m³·mol⁻¹ChemAxon
Polarizability21.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f72-7900000000-24d819c66c14ff8aeaf4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-4790000000-b3d6f7fd978638aee854JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-7940000000-ea0d584390fc83528ea7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0032-9300000000-9ea44ac5ab6994e2cbf1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9110000000-ffbac72bafb213d67f09JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-3b618e15250a28020451JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-574f7e21fceca4fa56a6JSpectraViewer | MoNA
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 IDFDB030557
KNApSAcK IDNot Available
Chemspider ID545
KEGG Compound IDC15650
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound561
PDB IDNot Available
ChEBI ID50604
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

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:
Not Available
Specific function:
Catalyzes the dehydration of methylthioribulose-1-phosphate (MTRu-1-P) into 2,3-diketo-5-methylthiopentyl-1-phosphate (DK-MTP-1-P). Functions in the methionine salvage pathway, which plays a key role in cancer, apoptosis, microbial proliferation and inflammation. May inhibit the CASP1-related inflammatory response (pyroptosis), the CASP9-dependent apoptotic pathway and the cytochrome c-dependent and APAF1-mediated cell death.
Gene Name:
APIP
Uniprot ID:
Q96GX9
Molecular weight:
27125.065
Reactions
5-Methylthioribulose 1-phosphate → 5-(Methylthio)-2,3-dioxopentyl phosphate + Waterdetails