alpha-D-Ribose 1-methylphosphonate 5-phosphate (ECMDB23846) (M2MDB005129)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (134)
Record Information
Version2.0
Creation Date2015-06-05 11:08:47 -0600
Update Date2015-08-05 16:22:05 -0600
Secondary Accession Numbers
  • ECMDB23846
Identification
Name:alpha-D-Ribose 1-methylphosphonate 5-phosphate
DescriptionAn organophosphate oxoanion obtained by deprotonation of the phosphate and phosphonate OH groups of α-D-ribose 1-methylphosphonate 5-phosphate; major species at pH 7.3.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • a-D-Ribose 1-methylphosphonate 5-phosphate
  • a-D-Ribose 1-methylphosphonic acid 5-phosphoric acid
  • alpha-D-Ribose 1-methylphosphonic acid 5-phosphoric acid
  • α-D-Ribose 1-methylphosphonate 5-phosphate
  • α-D-Ribose 1-methylphosphonic acid 5-phosphoric acid
Chemical Formula:C6H14O10P2
Weight:Average: 308.116
Monoisotopic: 308.006220647
InChI Key:RITBIFGLPRFTSB-KVTDHHQDSA-N
InChI:InChI=1S/C6H14O10P2/c1-17(9,10)16-6-5(8)4(7)3(15-6)2-14-18(11,12)13/h3-8H,2H2,1H3,(H,9,10)(H2,11,12,13)/t3-,4-,5-,6-/m1/s1
CAS number:Not Available
IUPAC Name:{[(2R,3S,4R,5R)-3,4-dihydroxy-5-{[hydroxy(methyl)phosphoryl]oxy}oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:[(2R,3S,4R,5R)-3,4-dihydroxy-5-{[hydroxy(methyl)phosphoryl]oxy}oxolan-2-yl]methoxyphosphonic acid
SMILES:CP(O)(=O)O[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Phosphonic acid ester
  • Alkyl phosphate
  • Organophosphonic acid derivative
  • Organophosphonic acid
  • Tetrahydrofuran
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organophosphorus compound
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility19.2 g/LALOGPS
logP-1.4ALOGPS
logP-2.7ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)0.96ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.98 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity54.23 m³·mol⁻¹ChemAxon
Polarizability23.93 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Water <> alpha-D-Ribose 1-methylphosphonate 5-phosphate + Pyrophosphate
alpha-D-Ribose 1-methylphosphonate 5-phosphate <> alpha-D-Ribose 1,2-cyclic phosphate 5-phosphate + Methane
alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Water > Hydrogen ion + Pyrophosphate + alpha-D-Ribose 1-methylphosphonate 5-phosphate
alpha-D-Ribose 1-methylphosphonate 5-phosphate > Methane + alpha-D-Ribose 1,2-cyclic phosphate 5-phosphate
alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Water <> alpha-D-Ribose 1-methylphosphonate 5-phosphate + Pyrophosphate
alpha-D-Ribose 1-methylphosphonate 5-phosphate <> alpha-D-Ribose 1,2-cyclic phosphate 5-phosphate + Methane
alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Water <> alpha-D-Ribose 1-methylphosphonate 5-phosphate + Pyrophosphate
alpha-D-Ribose 1-methylphosphonate 5-phosphate <> alpha-D-Ribose 1,2-cyclic phosphate 5-phosphate + Methane
SMPDB Pathways:
methylphosphonate degradation IPW002065 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Phosphonate and phosphinate metabolism ec00440
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9131000000-bc9dcc38732a7d9255c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-9371000000-1e28bd83f971f323cbe3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9300000000-290cffc4d0b6bf1f5bf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9113000000-66e49cfcd9ff3f8e194dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-34429d5aefa115435fd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c5b010e53053ea94db47View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID68820
HMDB IDNot Available
Pubchem Compound ID70678985
Kegg IDC20423
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Alpha-D-ribose 1-methylphosphonate 5-triphosphate diphosphatase
General function:
organic phosphonate catabolic process
Specific function:
Catalyzes the hydrolysis of alpha-D-ribose 1-methylphosphonate triphosphate (RPnTP) to form alpha-D-ribose 1-methylphosphonate phosphate (PRPn) and diphosphate.
Gene Name:
phnM
Uniprot ID:
P16689
Molecular weight:
42010
Reactions
Alpha-D-ribose 1-methylphosphonate 5-triphosphate + H(2)O = alpha-D-ribose 1-methylphosphonate 5-phosphate + diphosphate
Protein Details
2. Alpha-D-ribose 1-methylphosphonate 5-phosphate C-P lyase
General function:
organic phosphonate catabolic process
Specific function:
Catalyzes the breakage of the C-P bond in alpha-D-ribose 1-methylphosphonate 5-phosphate (PRPn) forming alpha-D-ribose 1,2-cyclic phosphate 5-phosphate (PRcP).
Gene Name:
phnJ
Uniprot ID:
P16688
Molecular weight:
31844
Reactions
Alpha-D-ribose 1-methylphosphonate 5-phosphate = alpha-D-ribose 1,2-cyclic phosphate 5-phosphate + methane