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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:38 UTC
HMDB IDHMDB00963
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Methylthioribose 1-phosphate
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).
Structure
Thumb
Synonyms
ValueSource
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 Weight260.202
Monoisotopic Molecular Weight260.011959972
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
CAS Registry Number72843-83-5
SMILES
CSCC1OC(OP(O)(O)=O)[C@H](O)[C@@H]1O
InChI Identifier
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)/t3?,4-,5-,6?/m1/s1
InChI KeyInChIKey=JTFITTQBRJDSTL-WATOWXBHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Organic phosphate
  • Monosaccharide
  • Saccharide
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-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
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Cystathionine Beta-Synthase DeficiencySMP00177Not Available
Glycine N-methyltransferase DeficiencySMP00222Not Available
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typeSMP00570Not Available
HypermethioninemiaSMP00341Not Available
Methionine Adenosyltransferase DeficiencySMP00221Not Available
Methionine MetabolismSMP00033map00270
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)SMP00340Not Available
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencySMP00214Not 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 IDFDB022341
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC04188
BioCyc IDCPD-444
BiGG ID43318
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00963
Metagene LinkHMDB00963
METLIN ID5909
PubChem Compound53477720
PDB IDNot Available
ChEBI ID27859
References
Synthesis ReferenceDella 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
General References
  1. Avila MA, Garcia-Trevijano ER, Lu SC, Corrales FJ, Mato JM: Methylthioadenosine. Int J Biochem Cell Biol. 2004 Nov;36(11):2125-30. [15313459 ]
  2. 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 ]
  3. Tisdale MJ: Methionine synthesis from 5'-methylthioadenosine by tumour cells. Biochem Pharmacol. 1983 Oct 1;32(19):2915-20. [6626263 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]

Enzymes

General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
Catalyzes the reversible phosphorylation of S-methyl-5'-thioadenosine (MTA) to adenine and 5-methylthioribose-1-phosphate. Involved in the breakdown of MTA, a major by-product of polyamine biosynthesis. Responsible for the first step in the methionine salvage pathway after MTA has been generated from S-adenosylmethionine. Has broad substrate specificity with 6-aminopurine nucleosides as preferred substrates.
Gene Name:
MTAP
Uniprot ID:
Q13126
Molecular weight:
31235.76
Reactions
5'-Methylthioadenosine + Phosphoric acid → Adenine + 5-Methylthioribose 1-phosphatedetails
General function:
Not Available
Specific function:
Catalyzes the interconversion of methylthioribose-1-phosphate (MTR-1-P) into methylthioribulose-1-phosphate (MTRu-1-P). Independently from catalytic activity, promotes cell invasion in response to constitutive RhoA activation by promoting FAK tyrosine phosphorylation and stress fiber turnover.
Gene Name:
MRI1
Uniprot ID:
Q9BV20
Molecular weight:
39149.38
Reactions
5-Methylthioribose 1-phosphate → 5-Methylthioribulose 1-phosphatedetails