alpha-D-Ribose 1-methylphosphonate 5-triphosphate (ECMDB23845) (M2MDB005128)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (5)Transporters (1)XML
Proteins (293)
Record Information
Version2.0
Creation Date2015-06-05 11:08:45 -0600
Update Date2015-09-14 16:46:23 -0600
Secondary Accession Numbers
  • ECMDB23845
Identification
Name:alpha-D-Ribose 1-methylphosphonate 5-triphosphate
DescriptionIn E. coli, alpha-D-Ribose 1-methylphosphonate 5-triphosphate is an intermediate in the transformation of Phosphonates to Phosphate. The enzyme alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase (EC 2.7.8.37) catalyses the reaction ATP + methylphosphonate <=> alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine (PMID: 22089136).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • a-D-Ribose 1-methylphosphonate 5-triphosphate
  • a-D-Ribose 1-methylphosphonic acid 5-triphosphoric acid
  • alpha-D-Ribose 1-methylphosphonic acid 5-triphosphoric acid
  • α-D-Ribose 1-methylphosphonate 5-triphosphate
  • α-D-Ribose 1-methylphosphonic acid 5-triphosphoric acid
Chemical Formula:C6H16O16P4
Weight:Average: 468.073
Monoisotopic: 467.938882427
InChI Key:UXNHAIRVTPGNPL-KVTDHHQDSA-N
InChI:InChI=1S/C6H16O16P4/c1-23(9,10)20-6-5(8)4(7)3(19-6)2-18-25(14,15)22-26(16,17)21-24(11,12)13/h3-8H,2H2,1H3,(H,9,10)(H,14,15)(H,16,17)(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}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name:({[(2R,3S,4R,5R)-3,4-dihydroxy-5-{[hydroxy(methyl)phosphoryl]oxy}oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
SMILES:CP(O)(=O)O[C@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(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:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility11.9 g/LALOGPS
logP-0.04ALOGPS
logP-3.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.75ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area256.04 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity75.98 m³·mol⁻¹ChemAxon
Polarizability32.87 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
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
Adenosine triphosphate + Methylphosphonate <> alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Adenine
Methylphosphonate + Adenosine triphosphate > Adenine + alpha-D-Ribose 1-methylphosphonate 5-triphosphate
alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Water > Hydrogen ion + Pyrophosphate + alpha-D-Ribose 1-methylphosphonate 5-phosphate
alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Water <> alpha-D-Ribose 1-methylphosphonate 5-phosphate + Pyrophosphate
Adenosine triphosphate + Methylphosphonate <> alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Adenine
alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Water <> alpha-D-Ribose 1-methylphosphonate 5-phosphate + Pyrophosphate
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_5_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9113200000-0281d4d58743ac3e86f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kd-8797100000-c8d7c9854872d0386784View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9210000000-162633a48b446e3d4360View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-9020600000-139809b27af9f7963786View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9120000000-49f2e4c84949bce8c2c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-ca51af04e235c66ccc2dView 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 ID68824
HMDB IDNot Available
Pubchem Compound ID70678978
Kegg IDC20422
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-triphosphate synthase subunit PhnL
General function:
organic phosphonate catabolic process
Specific function:
Together with PhnG, PhnH and PhnI is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
Gene Name:
phnL
Uniprot ID:
P16679
Molecular weight:
24705
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine
Protein Details
3. Alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnI
General function:
organic phosphonate catabolic process
Specific function:
Together with PhnG, PhnH and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate. PhnI alone has nucleosidase activity, catalyzing the hydrolysis of ATP or GTP forming alpha-D-ribose 5-triphosphate and adenine or guanine, respectively.
Gene Name:
phnI
Uniprot ID:
P16687
Molecular weight:
38852
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine
Protein Details
4. Alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnH
General function:
organic phosphonate catabolic process
Specific function:
Together with PhnG, PhnI and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
Gene Name:
phnH
Uniprot ID:
P16686
Molecular weight:
21027
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine
Protein Details
5. Alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnG
General function:
organic phosphonate transport
Specific function:
Together with PhnH, PhnI and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
Gene Name:
phnG
Uniprot ID:
P16685
Molecular weight:
16539
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine

Transporters

Protein Details
1. Alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnG
General function:
organic phosphonate transport
Specific function:
Together with PhnH, PhnI and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
Gene Name:
phnG
Uniprot ID:
P16685
Molecular weight:
16539
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine