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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:26 UTC
HMDB IDHMDB0001087
Secondary Accession Numbers
  • HMDB01087
Metabolite Identification
Common Name5-Methylthioribose
Description5-Methylthioribose (CAS: 23656-67-9) belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. 5-Methylthioribose is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Methylthioribose exists in all living organisms, ranging from bacteria to humans. In humans, 5-methylthioribose is involved in the metabolic disorder called hypermethioninemia. Outside of the human body, 5-methylthioribose has been detected, but not quantified in, several different foods, such as alaska wild rhubarbs, common verbena, greenthread tea, pasta, and Irish moss. This could make 5-methylthioribose a potential biomarker for the consumption of these foods. 5-Methylthioribose is a metabolite of 5-methylthioribose-1-phosphate. It is a substrate of methylthioribose kinase (EC 2.7.1.100) in the methionine metabolism pathway (KEGG). It can be found in Escherichia (PMID: 4203512 ).
Structure
Thumb
Synonyms
ValueSource
S-Methyl-5-thio-D-riboseKegg
5-(Methylsulfanyl)-D-riboseKegg
5-(Methylsulphanyl)-D-riboseGenerator
5-Deoxy-5-(methylthio)riboseHMDB
5-Methylthio-D-riboseHMDB
S(5)-Methyl-5-thio-D-riboseHMDB
S5-Methyl-5-thio-D-riboseHMDB
5-MethylthioriboseHMDB
5-S-Methyl-5-thio-D-riboseHMDB
5-S-Methyl-5-thio-beta-D-ribofuranoseHMDB
5-S-Methyl-5-thio-β-D-ribofuranoseHMDB
S-Methyl-5-thio-D-ribofuranoseHMDB
Chemical FormulaC6H12O4S
Average Molecular Weight180.222
Monoisotopic Molecular Weight180.045629562
IUPAC Name(2R,3R,4S,5S)-5-[(methylsulfanyl)methyl]oxolane-2,3,4-triol
Traditional Name5-methylthio-D-ribose
CAS Registry Number624740-12-1
SMILES
CSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O4S/c1-11-2-3-4(7)5(8)6(9)10-3/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1
InChI KeyOLVVOVIFTBSBBH-KVTDHHQDSA-N
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
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Polyol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022418
KNApSAcK IDNot Available
Chemspider ID388938
KEGG Compound IDC03089
BioCyc IDCPD-560
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5995
PubChem Compound439904
PDB IDNot Available
ChEBI ID16895
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gianotti AJ, Tower PA, Sheley JH, Conte PA, Spiro C, Ferro AJ, Fitchen JH, Riscoe MK: Selective killing of Klebsiella pneumoniae by 5-trifluoromethylthioribose. Chemotherapeutic exploitation of the enzyme 5-methylthioribose kinase. J Biol Chem. 1990 Jan 15;265(2):831-7. [PubMed:2153115 ]
  2. Della Ragione F, Carteni-Farina M, Gragnaniello V, Schettino MI, Zappia V: Purification and characterization of 5'-deoxy-5'-methylthioadenosine phosphorylase from human placenta. J Biol Chem. 1986 Sep 15;261(26):12324-9. [PubMed:3091600 ]
  3. Carteni-Farina M, della Ragione F, Cacciapuoti G, Porcelli M, Zappia V: Transport and metabolism of 5'-methylthioadenosine in human erythrocytes. Biochim Biophys Acta. 1983 Jan 19;727(2):221-9. [PubMed:6838867 ]
  4. Schroeder HR, Barnes CJ, Bohinski RC, Mallette MF: Biological production of 5-methylthioribose. Can J Microbiol. 1973 Nov;19(11):1347-54. [PubMed:4203512 ]