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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:15:48 UTC
HMDB IDHMDB0001299
Secondary Accession Numbers
  • HMDB01299
Metabolite Identification
Common Name5-Methylthioribulose 1-phosphate
Description5-Methylthioribulose 1-phosphate is an intermediate in the methionine salvage pathway. It is a microbial metabolite produced by gut microbes during methionine generation from methylthioadenosine. The first step is the phosphorolysis of methylthioadenosine to 5-methylthioribose-1-phosphate and adenine by the enzyme 5-deoxy- 5-methylthioadenosine phosphorylase (methylthioadenosine phosphorylase); 5-methylthioribose-1-phosphate is then converted to 5-methylthioribulose-1-phosphate (PMID: 6725268 ). 5-Deoxy-5-methylthioadenosine (methylthioadenosine) is a metabolite of S-adenosyl-L-methionine formed during the synthesis of the polyamines, spermidine and spermine.
Structure
Data?1547234148
Synonyms
ValueSource
5-S-Methyl-1-O-phosphono-5-thio-D-ribuloseChEBI
5-(Methylsulfanyl)-D-ribulose 1-phosphateKegg
5-(Methylsulfanyl)-D-ribulose 1-phosphoric acidGenerator
5-(Methylsulphanyl)-D-ribulose 1-phosphateGenerator
5-(Methylsulphanyl)-D-ribulose 1-phosphoric acidGenerator
5-Methylthioribulose 1-phosphoric acidGenerator
1-Phospho-5-S-methylthioribuloseHMDB
1-PhosphomethylthioribuloseHMDB
1PMT-RibuloseHMDB
5-Methylthio-2-ribulose-1-phosphateHMDB
5-Methylthio-5-deoxy-D-ribulose 1-phosphateHMDB
5-Methylthio-5-deoxy-D-ribulose-1-phosphateHMDB
5-Methylthioribulose-1-phosphateHMDB
5-S-Methyl-5-thio-D-erythro-pent-2-ulose 1-(dihydrogen phosphate)HMDB
5-S-Methyl-5-thio-D-ribulose 1-(dihydrogen phosphate)HMDB
Methylthioribulose-1-phosphateHMDB
MTRu-1-pHMDB
S-Methyl-5-thio-D-ribulose 1-phosphateHMDB
1-PMT-RibuloseHMDB
Methylthioribulose 1-phosphateHMDB
Chemical FormulaC6H13O7PS
Average Molecular Weight260.202
Monoisotopic Molecular Weight260.011959972
IUPAC Name{[(3R,4S)-3,4-dihydroxy-5-(methylsulfanyl)-2-oxopentyl]oxy}phosphonic acid
Traditional Namemethylthioribulose-1-phosphate
CAS Registry Number86316-83-8
SMILES
CSC[C@@H](O)[C@@H](O)C(=O)COP(O)(O)=O
InChI Identifier
InChI=1S/C6H13O7PS/c1-15-3-5(8)6(9)4(7)2-13-14(10,11)12/h5-6,8-9H,2-3H2,1H3,(H2,10,11,12)/t5-,6+/m1/s1
InChI KeyCNSJRYUMVMWNMC-RITPCOANSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentGlycerone phosphates
Alternative Parents
Substituents
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Acyloin
  • Beta-hydroxy ketone
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • 1,2-diol
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Organosulfur compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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 Solubility19.3 g/LALOGPS
logP-0.43ALOGPS
logP-1.3ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity53.31 m³·mol⁻¹ChemAxon
Polarizability22.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01w1-9710000000-da3fc8534da2cd8957f4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-7973000000-51639c96fd3e70d14bf8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-3590000000-48a371cabc865281cedbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pc-3920000000-0f483ba04442297b4622JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000g-9300000000-6e02d97a8ab3c704f801JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9310000000-4f7b1426b6d9f8a88ffaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9100000000-1e987229b4853fb45072JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fe6a484561738ead9cd1JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022541
KNApSAcK IDNot Available
Chemspider ID152225
KEGG Compound IDC04582
BioCyc IDNot Available
BiGG ID44103
Wikipedia LinkNot Available
METLIN ID6143
PubChem Compound174549
PDB IDNot Available
ChEBI ID28096
References
Synthesis ReferenceImker, Heidi J.; Fedorov, Alexander A.; Fedorov, Elena V.; Almo, Steven C.; Gerlt, John A. Mechanistic Diversity in the RuBisCO Superfamily: The "Enolase" in the Methionine Salvage Pathway in Geobacillus kaustophilus. Biochemistry (2007), 46(13), 4077-4089.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]

Enzymes

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
General function:
Not Available
Specific function:
Catalyzes the dehydration of methylthioribulose-1-phosphate (MTRu-1-P) into 2,3-diketo-5-methylthiopentyl-1-phosphate (DK-MTP-1-P). Functions in the methionine salvage pathway, which plays a key role in cancer, apoptosis, microbial proliferation and inflammation. May inhibit the CASP1-related inflammatory response (pyroptosis), the CASP9-dependent apoptotic pathway and the cytochrome c-dependent and APAF1-mediated cell death.
Gene Name:
APIP
Uniprot ID:
Q96GX9
Molecular weight:
27125.065
Reactions
5-Methylthioribulose 1-phosphate → 5-(Methylthio)-2,3-dioxopentyl phosphate + Waterdetails