P. aeruginosa Metabolome Database: Ribose 1,5-bisphosphate (PAMDB000819)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000819

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

🔍MOL SDF PDB SMILES InChI View Structure

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

Average Molecular Weight:

310.0897

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Monosaccharides

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Monosaccharide phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Oxolane
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
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 mg/mL	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 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.71 m³·mol^-1	ChemAxon
Polarizability	22.81 Å³	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
α-D-ribose-1,2-cyclic-phosphate-5-phosphate + Water > Hydrogen ion + Ribose 1,5-bisphosphate
Water <> Ribose 1,5-bisphosphate
Ribose 1,5-bisphosphate + Adenosine triphosphate + Ribose 1,5-bisphosphate > Adenosine diphosphate + Phosphoribosyl pyrophosphate + ADP

Pathways:

Pentose phosphate pathway pae00030
Phosphonate and phosphinate metabolism pae00440

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

Ribose 1,5-bisphosphate (PAMDB000819)

Structure for Ribose 1,5-bisphosphate (PAMDB000819)