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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-08-16 03:35:48 UTC
HMDB IDHMDB0001087
Secondary Accession Numbers
  • HMDB01087
Metabolite Identification
Common Name5-Methylthioribose
Description5-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).
Structure
Thumb
Synonyms
ValueSource
S-Methyl-5-thio-D-riboseKegg
5-Deoxy-5-(methylthio)riboseHMDB
5-methylthio-D-RiboseHMDB
S(5)-Methyl-5-thio-D-riboseHMDB
S5-Methyl-5-thio-D-riboseHMDB
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 Number23656-67-9
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
DescriptionThis compound belongs to the class of chemical entities known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Oxolane
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility176.0 mg/mLALOGPS
logP-1.4ALOGPS
logP-0.82ChemAxon
logS-0.01ALOGPS
pKa (Strongest Acidic)11.31ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.79 m3·mol-1ChemAxon
Polarizability17.75 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-7914d8991b0a6af1d99fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ai-2900000000-e36191d55523024bf643View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvj-9500000000-94cbb1e527c7c7e21314View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-21073f76322842d53a46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-89d811f24fdb17e739e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-ed328bd35b3fe1440450View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022418
KNApSAcK IDNot Available
Chemspider ID388938
KEGG Compound IDC03089
BioCyc IDCPD-560
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0001087
METLIN ID5995
PubChem Compound439904
PDB IDNot Available
ChEBI ID16895
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 ]