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Identification
YMDB IDYMDB00129
Name5-Methylthioribulose 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Methylthioribulose 1-phosphate, also known as 1PMT-ribulose or 1-phospho-5-S-methylthioribulose, belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position. 5-Methylthioribulose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Methylthioribulose 1-phosphate exists in all living species, ranging from bacteria to humans. Within yeast, 5-methylthioribulose 1-phosphate participates in a number of enzymatic reactions. In particular, 5-methylthioribulose 1-phosphate can be converted into 5-(methylthio)-2,3-dioxopentyl phosphate; which is catalyzed by the enzyme methylthioribulose-1-phosphate dehydratase. In addition, 5-methylthioribulose 1-phosphate can be biosynthesized from 5-methylthioribose 1-phosphate; which is catalyzed by the enzyme methylthioribose-1-phosphate isomerase. In yeast, 5-methylthioribulose 1-phosphate is involved in the metabolic pathway called the methionine metabolism and salvage pathway.
Structure
Thumb
Synonyms
  • 1-phospho-5-S-methylthioribulose
  • 1-phosphomethylthioribulose
  • 1PMT-ribulose
  • 5-methylthio-2-ribulose-1-phosphate
  • 5-Methylthio-5-deoxy-D-ribulose 1-phosphate
  • 5-methylthio-5-deoxy-D-ribulose-1-phosphate
  • 5-Methylthioribulose 1-phosphate
  • 5-Methylthioribulose 1-phosphic acid
  • 5-methylthioribulose-1-phosphate
  • 5-S-methyl-1-O-phosphono-5-thio-D-ribulose
  • 5-S-methyl-5-thio-D-erythro-pent-2-ulose 1-(dihydrogen phosphate)
  • 5-S-methyl-5-thio-D-ribulose 1-(dihydrogen phosphate)
  • methylthioribulose-1-phosphate
  • MTRu-1-P
  • S-Methyl-5-thio-D-ribulose 1-phosphate
  • 5-(Methylsulfanyl)-D-ribulose 1-phosphate
  • 5-(Methylsulfanyl)-D-ribulose 1-phosphoric acid
  • 5-(Methylsulphanyl)-D-ribulose 1-phosphate
  • 5-(Methylsulphanyl)-D-ribulose 1-phosphoric acid
  • 5-Methylthioribulose 1-phosphoric acid
  • 1-PMT-Ribulose
  • Methylthioribulose 1-phosphate
CAS number86316-83-8
WeightAverage: 260.202
Monoisotopic: 260.011959972
InChI KeyCNSJRYUMVMWNMC-RITPCOANSA-N
InChIInChI=1S/C6H13O7PS/c1-15-3-5(8)6(9)4(7)2-13-14(10,11)12/h5-6,8-9H,2-3H2,1H3,(H2,10,11,12)/t5-,6+/m1/s1
IUPAC Name{[(3R,4S)-3,4-dihydroxy-5-(methylsulfanyl)-2-oxopentyl]oxy}phosphonic acid
Traditional IUPAC Namemethylthioribulose-1-phosphate
Chemical FormulaC6H13O7PS
SMILES[H]O[C@@]([H])(C(=O)C([H])([H])OP(=O)(O[H])O[H])[C@]([H])(O[H])C([H])([H])SC([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentGlycerone phosphates
Alternative Parents
Substituents
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Acyloin
  • Beta-hydroxy ketone
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • 1,2-diol
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Organosulfur compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Solubility19.3 g/LALOGPS
logP-0.43ALOGPS
logP-1.3ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity53.31 m³·mol⁻¹ChemAxon
Polarizability22.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
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
5-Methylthioribulose 1-phosphate5-(methylsulfanyl)-2,3-dioxopentyl phosphate + water
5-Methylthioribose 1-phosphate5-Methylthioribulose 1-phosphate
KEGG Reactions
5-Methylthioribulose 1-phosphate5-(methylsulfanyl)-2,3-dioxopentyl phosphate + water
S-Methyl-5-thio-alpha-D-ribose 1-phosphate5-Methylthioribulose 1-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01w1-9710000000-da3fc8534da2cd8957f4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-7973000000-51639c96fd3e70d14bf8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-3590000000-48a371cabc865281cedbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pc-3920000000-0f483ba04442297b4622JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000g-9300000000-6e02d97a8ab3c704f801JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9310000000-4f7b1426b6d9f8a88ffaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9100000000-1e987229b4853fb45072JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fe6a484561738ead9cd1JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Pirkov, I., Norbeck, J., Gustafsson, L., Albers, E. (2008). "A complete inventory of all enzymes in the eukaryotic methionine salvage pathway." FEBS J 275:4111-4120.18625006
Synthesis Reference:Imker, Heidi J.; Fedorov, Alexander A.; Fedorov, Elena V.; Almo, Steven C.; Gerlt, John A. Mechanistic Diversity in the RuBisCO Superfamily: The "Enolase" in the Methionine Salvage Pathway in Geobacillus kaustophilus. Biochemistry (2007), 46(13), 4
External Links:
ResourceLink
CHEBI ID28096
HMDB IDHMDB01299
Pubchem Compound ID329
Kegg IDC04582
ChemSpider ID152225
FOODB IDFDB022541
Wikipedia IDNot Available
BioCyc IDCPD-1063

Enzymes

General function:
Involved in metal ion binding
Specific function:
Catalyzes the dehydration of methylthioribulose-1- phosphate (MTRu-1-P) into 2,3-diketo-5-methylthiopentyl-1- phosphate (DK-MTP-1-P)
Gene Name:
MDE1
Uniprot ID:
P47095
Molecular weight:
27426.59961
Reactions
S-methyl-5-thio-D-ribulose 1-phosphate → 5-(methylthio)-2,3-dioxopentyl phosphate + H(2)O.
General function:
Involved in cellular metabolic process
Specific function:
Catalyzes the interconversion of methylthioribose-1- phosphate (MTR-1-P) into methylthioribulose-1-phosphate (MTRu-1- P)
Gene Name:
MRI1
Uniprot ID:
Q06489
Molecular weight:
45019.89844
Reactions
S-methyl-5-thio-alpha-D-ribose 1-phosphate → S-methyl-5-thio-D-ribulose 1-phosphate.