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Record Information
Version	2.0
Creation Date	2012-05-31 14:20:33 -0600
Update Date	2015-09-17 15:41:45 -0600
Secondary Accession Numbers	ECMDB11688
Identification
Name:	Ribose 1,5-bisphosphate
Description	Ribose 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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa7cbb7d4> Close
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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Pentose phosphates
Alternative Parents	Monosaccharide phosphates Monoalkyl phosphates Tetrahydrofurans Secondary alcohols 1,2-diols Oxacyclic compounds Organic oxides Hydrocarbon derivatives
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 Framework	Aliphatic heteromonocyclic compounds
External Descriptors	ribose bisphosphate (CHEBI:17994 )
Physical Properties
State:	Solid
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 15.6 g/L ALOGPS logP -1.4 ALOGPS logP -2.5 ChemAxon logS -1.3 ALOGPS pKa (Strongest Acidic) 0.89 ChemAxon pKa (Strongest Basic) -3.7 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 183.21 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 51.71 m³·mol⁻¹ ChemAxon Polarizability 22.81 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 Biosynthesis PW000909 methylphosphonate degradation I PW002065
KEGG Pathways:	Pentose phosphate pathway ec00030 Phosphonate and phosphinate metabolism ec00440
EcoCyc Pathways:	PRPP biosynthesis II PWY0-661 methylphosphonate degradation PWY0-1533
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0002-9242000000-8774eefa87ec8d718d96 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-9250000000-82ae01a7fb604ac98e45 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0002-9300000000-8e97532fccf4f554c8a9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a6r-9217000000-beaa35bde8583c9e80b9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9010000000-68c77d583be94b04949e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-2e63a6fcb5a41e8c8acb View 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
Links
External Links:	Resource Link CHEBI ID 17994 HMDB ID HMDB11688 Pubchem Compound ID 3036640 Kegg ID C01151 ChemSpider ID 26328792 Wikipedia ID Not Available BioCyc ID RIBOSE-15-BISPHOSPHATE EcoCyc ID RIBOSE-15-BISPHOSPHATE

Enzymes