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5-Methylthioribose 1-phosphate (YMDB00040)

Identification
YMDB IDYMDB00040
Name5-Methylthioribose 1-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Methylthioribose 1-phosphate, also known as 1-phospho-5-S-methylthioribose or D-ribofuranoside, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. 5-Methylthioribose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Within yeast, 5-methylthioribose 1-phosphate participates in a number of enzymatic reactions. In particular, 5-methylthioribose 1-phosphate can be converted into 5-methylthioribulose 1-phosphate; which is catalyzed by the enzyme methylthioribose-1-phosphate isomerase. In addition, 5-methylthioribose 1-phosphate and adenine can be biosynthesized from 5'-S-methyl-5'-thioadenosine through its interaction with the enzyme 5'-methylthioadenosine phosphorylase. In yeast, 5-methylthioribose 1-phosphate is involved in the metabolic pathway called the methionine metabolism and salvage pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 1-phospho-5-S-methylthioribose
  • 1-phosphomethylthioribose
  • 5-Methylthio-5-deoxy-D-ribose 1-phosphate
  • 5-methylthio-5-deoxy-D-ribose-1-phosphate
  • 5-methylthio-D-ribose-1-phosphate
  • 5-Methylthioribose 1-phosphate
  • 5-Methylthioribose 1-phosphic acid
  • 5-methylthioribose-1-phosphate
  • D-ribofuranoside
  • S-methyl-5-thio-alpha-D-ribose 1-phosphate
  • S5-methyl-5-thio-D-ribose-1-phosphate
  • 5-Methylthioribose 1-phosphoric acid
CAS number72843-83-5
WeightAverage: 260.202
Monoisotopic: 260.011959972
InChI KeyJTFITTQBRJDSTL-WATOWXBHSA-N
InChIInChI=1S/C6H13O7PS/c1-15-2-3-4(7)5(8)6(12-3)13-14(9,10)11/h3-8H,2H2,1H3,(H2,9,10,11)/t3?,4-,5-,6?/m1/s1
IUPAC Name{[(3R,4S)-3,4-dihydroxy-5-[(methylsulfanyl)methyl]oxolan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name[(3R,4S)-3,4-dihydroxy-5-[(methylsulfanyl)methyl]oxolan-2-yl]oxyphosphonic acid
Chemical FormulaC6H13O7PS
SMILES[H]O[C@@]1([H])C([H])(OP(=O)(O[H])O[H])OC([H])(C([H])([H])SC([H])([H])[H])[C@@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetrahydrofuran
  • 1,2-diol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility28.7 g/LALOGPS
logP-1.2ALOGPS
logP-0.94ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.67 m³·mol⁻¹ChemAxon
Polarizability22.53 ųChemAxon
Number of Rings1ChemAxon
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-Methylthioribose 1-phosphate → 5-Methylthioribulose 1-phosphate
phosphate + 5'-S-methyl-5'-thioadenosine → 5-Methylthioribose 1-phosphate + Adenine
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, Positivesplash10-0002-9100000000-2488064947bfab511f5eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-9011000000-4ba10accddc39548ffacJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9340000000-81076180aee84a287f34JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9330000000-16cc1e6103ea1cca9414JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-9200000000-e1e1c3a051f24524c0f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9010000000-6e1ba60f11f69a1cb95aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-138587ed5d90d657c9c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-41783131ed46fc1d13e5JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Bumann, M., Djafarzadeh, S., Oberholzer, A. E., Bigler, P., Altmann, M., Trachsel, H., Baumann, U. (2004). "Crystal structure of yeast Ypr118w, a methylthioribose-1-phosphate isomerase related to regulatory eIF2B subunits." J Biol Chem 279:37087-37094.15215245
  • 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
  • Marchitto, K. S., Ferro, A. J. (1985). "The metabolism of 5'-methylthioadenosine and 5-methylthioribose 1-phosphate in Saccharomyces cerevisiae." J Gen Microbiol 131:2153-2164.3906034
Synthesis Reference:Della Ragione, Fulvio; Carteni-Farina, Maria; Gragnaniello, Vincenzo; Schettino, Maria Irene; Zappia, Vincenzo. Purification and characterization of 5'-deoxy-5'-methylthioadenosine phosphorylase from human placenta. Journal of Biological Chemistry (1
External Links:
ResourceLink
CHEBI ID27859
HMDB IDHMDB0000963
Pubchem Compound ID465
Kegg IDC04188
ChemSpider IDNot Available
FOODB IDFDB022341
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Methylthioribose-1-phosphate isomerase
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.
Protein Details
2. Multicopy enhancer of UAS2
General function:
Involved in catalytic activity
Specific function:
Seems to be implicated in the regulation of the expression of the ADH2 gene
Gene Name:
MEU1
Uniprot ID:
Q07938
Molecular weight:
37856.30078
Reactions
S-methyl-5'-thioadenosine + phosphate → adenine + S-methyl-5-thio-alpha-D-ribose 1-phosphate