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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:46 UTC
HMDB IDHMDB0000963
Secondary Accession Numbers
  • HMDB00963
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 KeyJTFITTQBRJDSTL-WATOWXBHSA-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
  • 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 FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-2488064947bfab511f5eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-9011000000-4ba10accddc39548ffacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9340000000-81076180aee84a287f34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9330000000-16cc1e6103ea1cca9414View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-9200000000-e1e1c3a051f24524c0f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9010000000-6e1ba60f11f69a1cb95aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-138587ed5d90d657c9c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-41783131ed46fc1d13e5View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Cystathionine Beta-Synthase DeficiencyPw000100Pw000100 greyscalePw000100 simpleNot Available
Glycine N-methyltransferase DeficiencyPw000103Pw000103 greyscalePw000103 simpleNot Available
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typePw000546Pw000546 greyscalePw000546 simpleNot Available
HypermethioninemiaPw000101Pw000101 greyscalePw000101 simpleNot Available
Methionine Adenosyltransferase DeficiencyPw000105Pw000105 greyscalePw000105 simpleNot Available
Displaying entries 1 - 5 of 8 in total
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
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. [PubMed: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. [PubMed:6411330 ]
  3. Tisdale MJ: Methionine synthesis from 5'-methylthioadenosine by tumour cells. Biochem Pharmacol. 1983 Oct 1;32(19):2915-20. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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