5-Methylthioribose 1-phosphate (CHEM035008)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:24:53 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM035008
Identification
Common Name5-Methylthioribose 1-phosphate
ClassSmall Molecule
Description5-Methylthioribose 1-phosphate is an intermediate in methionine biosynthesis. It is converted from 5'-Deoxy-5'-methylthioadenosine by 5'-Deoxy-5'-methylthioadenosine phosphorylase. Then it is converted to methionine (PMID 2153115). In the methionine salvage pathway 5-methylthioribose 1-phosphate isomerase (M1Pi) catalyzes the conversion of 5-methylthioribose 1-phosphate (MTR-1-P) to 5-methylthioribulose 1-phosphate (MTRu-1-P)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Methylthioribose 1-phosphoric acidGenerator
1-Phospho-5-S-methylthioriboseHMDB
1-PhosphomethylthioriboseHMDB
5-Methylthio-5-deoxy-D-ribose 1-phosphateHMDB
5-Methylthio-5-deoxy-D-ribose-1-phosphateHMDB
5-Methylthio-D-ribose-1-phosphateHMDB
5-Methylthioribose-1-phosphateHMDB
D-RibofuranosideHMDB
S-Methyl-5-thio-alpha-D-ribose 1-phosphateHMDB
S5-Methyl-5-thio-D-ribose-1-phosphateHMDB
Chemical FormulaC6H13O7PS
Average Molecular Mass260.202 g/mol
Monoisotopic Mass260.012 g/mol
CAS Registry Number72843-83-5
IUPAC Name{[(3R,4S)-3,4-dihydroxy-5-[(methylsulfanyl)methyl]oxolan-2-yl]oxy}phosphonic acid
Traditional Name[(3R,4S)-3,4-dihydroxy-5-[(methylsulfanyl)methyl]oxolan-2-yl]oxyphosphonic acid
SMILESCSCC1OC(OP(O)(O)=O)[C@H](O)[C@@H]1O
InChI IdentifierInChI=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
InChI KeyJTFITTQBRJDSTL-WATOWXBHSA-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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-2488064947bfab511f5eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-9011000000-4ba10accddc39548ffacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9340000000-81076180aee84a287f34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9330000000-16cc1e6103ea1cca9414Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-9200000000-e1e1c3a051f24524c0f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9010000000-6e1ba60f11f69a1cb95aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-138587ed5d90d657c9c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-41783131ed46fc1d13e5Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000963
FooDB IDFDB022341
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID43318
BioCyc IDNot Available
METLIN ID5909
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID27859
PubChem Compound ID53477720
Kegg Compound IDC04188
YMDB IDYMDB00040
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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 (1986), 261(26), 12324-9.
2. Avila MA, Garcia-Trevijano ER, Lu SC, Corrales FJ, Mato JM: Methylthioadenosine. Int J Biochem Cell Biol. 2004 Nov;36(11):2125-30.
3. Savarese TM, Ghoda LY, Dexter DL, Parks RE Jr: Conversion of 5'-deoxy-5'-methylthioadenosine and 5'-deoxy-5'-methylthioinosine to methionine in cultured human leukemic cells. Cancer Res. 1983 Oct;43(10):4699-702.
4. Tisdale MJ: Methionine synthesis from 5'-methylthioadenosine by tumour cells. Biochem Pharmacol. 1983 Oct 1;32(19):2915-20.
5. Savarese TM, Cannistra AJ, Parks RE Jr, Secrist JA 3rd, Shortnacy AT, Montgomery JA: 5'-deoxy-5'-methylthioadenosine phosphorylase--IV. Biological activity of 2-fluoroadenine-substituted 5'-deoxy-5'-methylthioadenosine analogs. Biochem Pharmacol. 1987 Jun 15;36(12):1881-93.
6. Ghoda LY, Savarese TM, Dexter DL, Parks RE Jr, Trackman PC, Abeles RH: Characterization of a defect in the pathway for converting 5'-deoxy-5'-methylthioadenosine to methionine in a subline of a cultured heterogeneous human colon carcinoma. J Biol Chem. 1984 Jun 10;259(11):6715-9.
7. 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.