S-methyl-5-thio-α-D-ribose 1-phosphate (PAMDB120411)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120411
Identification
Name: S-methyl-5-thio-α-D-ribose 1-phosphate
Description:Dianion of S-methyl-5-thio-α-D-ribose 1-phosphate.
Structure
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🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 5-methylthioribose-1-phosphate
  • S5-methyl-5-thio-D-ribose-1-phosphate
  • 5-methylthio-D-ribose-1-phosphate
  • 5-MTR-1-P1-phosphomethylthioribose
  • 1-phospho-5-S-methylthioribose
  • 1-PMTR1-phospho-5-S-methylthio-α-D-ribofuranoside
  • S-methyl-5-thio-α-D-ribose 1-phosphate
  • S-methyl-5-thio-D-ribose 1-phosphate
Chemical Formula: C6H11O7PS
Average Molecular Weight: 258.182
Monoisotopic Molecular Weight: 260.01196
InChI Key: JTFITTQBRJDSTL-JDJSBBGDSA-L
InChI:InChI=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)/p-2/t3-,4-,5-,6?/m1/s1
CAS number: 72843-83-5
IUPAC Name:5-S-methyl-1-O-phosphonato-5-thio-α-D-ribofuranose
Traditional IUPAC Name: [(3R,4S)-3,4-dihydroxy-5-[(methylsulfanyl)methyl]oxolan-2-yl]oxyphosphonic acid
SMILES:CSCC1(OC(OP([O-])(=O)[O-])C(C1O)O)
Chemical Taxonomy
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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic oxygen compounds
Sub ClassOrganooxygen compounds
Direct Parent Pentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Oxolane
  • 1,2-diol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility28.7 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.67 m3·mol-1ChemAxon
Polarizability22.53 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
S-methyl-5-thio-α-D-ribose 1-phosphate → 5-methylthioribulose 1-phosphate
5'-Methylthioadenosine + phosphate → Adenine + S-methyl-5-thio-α-D-ribose 1-phosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
References:
  • Avila MA, Garcia-Trevijano ER, Lu SC, Corrales FJ, Mato JM: Methylthioadenosine. Int J Biochem Cell Biol. 2004 Nov;36(11):2125-30. [15313459 ]
  • 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. [6411330 ]
  • Tisdale MJ: Methionine synthesis from 5'-methylthioadenosine by tumour cells. Biochem Pharmacol. 1983 Oct 1;32(19):2915-20. [6626263 ]
  • 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. [3109431 ]
  • 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. [6725268 ]
  • 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. [2153115 ]
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 (1986), 261(26), 12324-9.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
METABOLIGHTSMTBLC58533
HMDBHMDB00963
BIGG43318
CHEBI58533
PUBCHEM52940236
LIGAND-CPDC04188