Ribose 1,5-bisphosphate (ECMDB11688) (M2MDB000819)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (682)
Record Information
Version2.0
Creation Date2012-05-31 14:20:33 -0600
Update Date2015-09-17 15:41:45 -0600
Secondary Accession Numbers
  • ECMDB11688
Identification
Name:Ribose 1,5-bisphosphate
DescriptionRibose 1,5-bisphosphate (Rib-1,5-P2), a newly discovered activator of phosphofructokinase. It forms rapidly during the initiation of glycolytic flux and disappears within 20 s/ Ribose 1,5-bisphosphate is a potent regulator of the fructose 6-phosphate/fructose 1,6-bisphosphate cycle. Ribose 1,5-bisphosphate is a substrate for Ribose 1,5-bisphosphate phosphokinase (EC 2.7.4.23), an enzyme that catalyzes the chemical reaction.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • D-Ribose 1,5-bisphosphate
  • D-Ribose 1,5-bisphosphoric acid
  • D-Ribose 1,5-diphosphate
  • D-Ribose 1,5-diphosphoric acid
  • R1,5P
  • Rib-1,5-P2
  • Ribose 1,5-bisphosphoric acid
Chemical Formula:C5H12O11P2
Weight:Average: 310.0897
Monoisotopic: 309.98548425
InChI Key:AAAFZMYJJHWUPN-TXICZTDVSA-N
InChI:InChI=1S/C5H12O11P2/c6-3-2(1-14-17(8,9)10)15-5(4(3)7)16-18(11,12)13/h2-7H,1H2,(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1
CAS number:14689-84-0
IUPAC Name:{[(3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name:ribose 1,5-bisphosphate
SMILES:O[C@H]1[C@@H](O)[C@@H](OP(O)(O)=O)O[C@@H]1COP(O)(O)=O
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
  • Alkyl phosphate
  • Phosphoric acid ester
  • Tetrahydrofuran
  • 1,2-diol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility15.6 g/LALOGPS
logP-1.4ALOGPS
logP-2.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.21 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity51.71 m³·mol⁻¹ChemAxon
Polarizability22.81 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Ribose 1,5-bisphosphate <> ADP + Phosphoribosyl pyrophosphate
Ribose-1-phosphate + Adenosine triphosphate > Hydrogen ion + Ribose 1,5-bisphosphate + ADP
&alpha;-D-ribose-1,2-cyclic-phosphate-5-phosphate + Water > Hydrogen ion + Ribose 1,5-bisphosphate
Ribose 1,5-bisphosphate + Adenosine triphosphate > Phosphoribosyl pyrophosphate + ADP
Water <> Ribose 1,5-bisphosphate
Ribose 1,5-bisphosphate + Adenosine triphosphate + Ribose 1,5-bisphosphate > Adenosine diphosphate + Phosphoribosyl pyrophosphate + ADP
alpha-D-Ribose 1,2-cyclic phosphate 5-phosphate + Water > Hydrogen ion + Ribose 1,5-bisphosphate
SMPDB Pathways:
PRPP BiosynthesisPW000909 ThumbThumb?image type=greyscaleThumb?image type=simple
methylphosphonate degradation IPW002065 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Pentose phosphate pathway ec00030
  • Phosphonate and phosphinate metabolism ec00440
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9242000000-8774eefa87ec8d718d96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9250000000-82ae01a7fb604ac98e45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9300000000-8e97532fccf4f554c8a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9217000000-beaa35bde8583c9e80b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-68c77d583be94b04949eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-2e63a6fcb5a41e8c8acbView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17994
HMDB IDHMDB11688
Pubchem Compound ID3036640
Kegg IDC01151
ChemSpider ID26328792
Wikipedia IDNot Available
BioCyc IDRIBOSE-15-BISPHOSPHATE
EcoCyc IDRIBOSE-15-BISPHOSPHATE

Enzymes

Protein Details
1. Phosphopentomutase
General function:
Involved in catalytic activity
Specific function:
Phosphotransfer between the C1 and C5 carbon atoms of pentose
Gene Name:
deoB
Uniprot ID:
P0A6K6
Molecular weight:
44370
Reactions
Alpha-D-ribose 1-phosphate = D-ribose 5-phosphate.
2-deoxy-alpha-D-ribose 1-phosphate = 2-deoxy-alpha-D-ribose 5-phosphate.
Protein Details
2. ATP-binding protein phnN
General function:
Involved in protein binding
Specific function:
Belongs to an operon involved in alkylphosphonate uptake and C-P lyase. Exact function not known
Gene Name:
phnN
Uniprot ID:
P16690
Molecular weight:
20729
Reactions
ATP + ribose 1,5-bisphosphate = ADP + 5-phospho-alpha-D-ribose 1-diphosphate.
Protein Details
3. Phosphoglucomutase
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose
Gene Name:
pgm
Uniprot ID:
P36938
Molecular weight:
58361
Reactions
Alpha-D-glucose 1-phosphate = alpha-D-glucose 6-phosphate.
Protein Details
4. Phosphoribosyl 1,2-cyclic phosphodiesterase
General function:
organic phosphonate catabolic process
Specific function:
Catalyzes the hydrolysis of the cyclic ribose-phosphate to form alpha-D-ribose 1,5-bisphosphate.
Gene Name:
phnP
Uniprot ID:
P16692
Molecular weight:
27847
Reactions
5-phospho-alpha-D-ribose 1,2-cyclic phosphate + H(2)O = alpha-D-ribose 1,5-bisphosphate