Record Information
Version2.0
Creation Date2012-05-31 14:40:08 -0600
Update Date2015-07-07 11:22:39 -0600
Secondary Accession Numbers
  • ECMDB20344
Identification
Name:beta-D-Ribopyranose
DescriptionBeta-D-ribopyranose is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Ribose 5-phosphate is involved in the pentose phosphate pathway and ribose degradation. The pentose phosphate pathway plays several key roles in metabolism including supply of biosynthetic carbon skeletons and reducing power. (PMID 9546650) Ribose-5-phosphate isomerase A (RpiA) plays an important role in interconverting between ribose-5-phosphate (R5P) and ribulose-5-phosphate in the pentose phosphate pathway and the Calvin cycle. (PMID 19214439). In Escherichia coli, RpiA catalyzes the interconversion of ribose-5-phosphate and ribulose-5-phosphate and is a key enzyme in the pentose phosphate pathway. (PMID 12182339).
Structure
Thumb
Synonyms:
  • 5-(Dihydrogen phosphate)D-Ribose
  • 5-(Dihydrogen phosphoric acid)D-ribose
  • 5-O-Phosphono-D-ribose
  • b-D-Ribopyranose
  • D-Ribofuranose, 5-(dihydrogen phosphate)
  • D-Ribofuranose, 5-(dihydrogen phosphoric acid)
  • D-Ribose
  • D-Ribose 5-(dihydrogen phosphate)
  • D-Ribose 5-(dihydrogen phosphoric acid)
  • D-Ribose 5-phosphate
  • D-Ribose 5-phosphoric acid
  • D-Ribose, 5-(dihydrogen phosphate)
  • D-Ribose, 5-(dihydrogen phosphoric acid)
  • D-Ribose-5-P
  • D-Ribose-5-phosphate
  • D-Ribose-5-phosphorate
  • D-Ribose-5-phosphoric acid
  • Pentose
  • Ribose
  • Ribose 5-monophosphate
  • Ribose 5-monophosphoric acid
  • Ribose 5-phosphate
  • Ribose 5-phosphoric acid
  • Ribose phosphate
  • Ribose phosphoric acid
  • Ribose, 5-(dihydrogen phosphate)
  • Ribose, 5-(dihydrogen phosphoric acid)
  • Ribose-5-P
  • Ribose-5-phosphate
  • Ribose-5-phosphorate
  • Ribose-5-phosphoric acid
  • Ribose-5P
  • β-D-Ribopyranose
Chemical Formula:C5H10O5
Weight:Average: 150.1299
Monoisotopic: 150.05282343
InChI Key:SRBFZHDQGSBBOR-TXICZTDVSA-N
InChI:InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4-,5-/m1/s1
CAS number:50-69-1
IUPAC Name:(2R,3R,4R,5R)-oxane-2,3,4,5-tetrol
Traditional IUPAC Name:β-D-ribopyranose
SMILES:O[C@@H]1CO[C@@H](O)[C@H](O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:95 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1220 g/LALOGPS
logP-2.6ALOGPS
logP-2.3ChemAxon
logS0.91ALOGPS
pKa (Strongest Acidic)11.31ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.96 m³·mol⁻¹ChemAxon
Polarizability13.23 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Ribose DegradationPW002102 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
260± 21 uMK120.2 g/L NH4Cl, 2.0 g/L (NH4)2SO4, 3.25 g/L KH2PO4, 2.5 g/L K2HPO4, 1.5 g/L NaH2PO4, 0.5 g/L MgSO4; trace substances: 10 mg/L CaCl2, 0.5 mg/L ZnSO4, 0.25 mg/L CuCl2, 0.25 mg/L MnSO4, 0.175 mg/L CoCl2, 0.125 mg/L H3BO3, 2.5 mg/L AlCl3, 0.5 mg/L Na2MoO4, 10Stationary Phase, glucose limitedBioreactor, pH controlled, aerated, dilution rate=0.125 L/h37 oCPMID: 11488613
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9400000000-f20d1c35a7eeea1609a5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00g0-9256300000-ae2d57025e3828494249View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-1900000000-07783f4be8db8a14f6f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-1900000000-eebbf905b1ed94cebf13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cka-9100000000-9f3469ad5a1c8e425555View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2900000000-3482c4e67045ff82c4f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-4900000000-aedd03247641e8491448View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b0a8f8b59e745078a05eView in MoNA
References
References:
  • Buchholz, A., Takors, R., Wandrey, C. (2001). "Quantification of intracellular metabolites in Escherichia coli K12 using liquid chromatographic-electrospray ionization tandem mass spectrometric techniques." Anal Biochem 295:129-137. Pubmed: 11488613
  • 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
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27476
HMDB IDHMDB12194
Pubchem Compound ID441481
Kegg IDC08353
ChemSpider ID5575
Wikipedia IDNot Available
BioCyc IDCPD0-1110
EcoCyc IDCPD0-1110
Ligand ExpoRIP

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex RbsABCD involved in ribose import. Responsible for energy coupling to the transport system
Gene Name:
rbsA
Uniprot ID:
P04983
Molecular weight:
55041
Reactions
ATP + H(2)O + monosaccharide(Out) = ADP + phosphate + monosaccharide(In).
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for ribose. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
rbsC
Uniprot ID:
P0AGI1
Molecular weight:
33452
General function:
Involved in intramolecular lyase activity
Specific function:
Catalyzes the interconversion of beta-pyran and beta- furan forms of D-ribose. It also catalyzes the conversion between beta-allofuranose and beta-allopyranose
Gene Name:
rbsD
Uniprot ID:
P04982
Molecular weight:
15292
Reactions
Beta-D-ribopyranose = beta-D-ribofuranose.
Beta-D-allopyranose = beta-D-allofuranose.
General function:
Carbohydrate transport and metabolism
Specific function:
Involved in the high-affinity D-ribose membrane transport system and also serves as the primary chemoreceptor for chemotaxis
Gene Name:
rbsB
Uniprot ID:
P02925
Molecular weight:
30950

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex RbsABCD involved in ribose import. Responsible for energy coupling to the transport system
Gene Name:
rbsA
Uniprot ID:
P04983
Molecular weight:
55041
Reactions
ATP + H(2)O + monosaccharide(Out) = ADP + phosphate + monosaccharide(In).
General function:
Involved in transmembrane transport
Specific function:
Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs
Gene Name:
setC
Uniprot ID:
P31436
Molecular weight:
43493
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for ribose. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
rbsC
Uniprot ID:
P0AGI1
Molecular weight:
33452
General function:
Carbohydrate transport and metabolism
Specific function:
Involved in the high-affinity D-ribose membrane transport system and also serves as the primary chemoreceptor for chemotaxis
Gene Name:
rbsB
Uniprot ID:
P02925
Molecular weight:
30950