Ribose-1-phosphate (PAMDB000637)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000637
Identification
Name: Ribose-1-phosphate
Description:Ribose 1-phosphate is an intermediate in the metabolism of Pyrimidine and the metabolism of Nicotinate and nicotinamide. It is a substrate for Uridine phosphorylase 2, Phosphoglucomutase, Purine nucleoside phosphorylase and Uridine phosphorylase 1. Ribose 1-phosphate can be formed from guanosine through the action of purine nucleoside phosphorylase. Ribose 1-phosphate can also act as a ribose donor in the synthesis of xanthosine as catalyzed by the same enzyme (purine nucleoside phosphorylase). The presence of guanase, which irreversibly converts guanine to xanthine, affects the overall process of guanosine transformation. The activated ribose moiety in Ribose 1-phosphate which stems from the catabolism of purine nucleosides can be transferred to uracil and, in the presence of ATP, used for the synthesis of pyrimidine nucleotides; therefore, purine nucleosides can act as ribose donors for the salvage of pyrimidine bases.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • α-D-ribofuranose 1-phosphate
  • α-D-ribofuranose 1-phosphoric acid
  • α-D-ribose-1P
  • 1-O-Phosphono-D-ribofuranose
  • A-D-Ribofuranose 1-(dihydrogen phosphate)
  • a-D-Ribofuranose 1-(dihydrogen phosphoric acid)
  • a-D-Ribofuranose 1-phosphate
  • a-D-Ribofuranose 1-phosphoric acid
  • A-D-Ribose 1-phosphate
  • a-D-Ribose 1-phosphoric acid
  • a-D-Ribose-1P
  • Alpha-D-Ribofuranose 1-(dihydrogen phosphate)
  • alpha-D-Ribofuranose 1-(dihydrogen phosphoric acid)
  • Alpha-D-Ribofuranose 1-phosphate
  • alpha-D-Ribofuranose 1-phosphoric acid
  • Alpha-D-Ribose 1-phosphate
  • alpha-D-Ribose 1-phosphoric acid
  • Alpha-D-Ribose-1P
  • D-Ribofuranose 1-(dihydrogen phosphate)
  • D-Ribofuranose 1-(dihydrogen phosphoric acid)
  • D-Ribofuranose 1-phosphate
  • D-Ribofuranose 1-phosphoric acid
  • D-Ribose-1-phosphate
  • D-Ribose-1-phosphoric acid
  • D-Ribose-1P
  • Ribofuranose 1-phosphate
  • Ribofuranose 1-phosphoric acid
  • Ribose 1-phosphate
  • Ribose 1-phosphoric acid
  • Ribose-1-phosphate
  • Ribose-1-phosphoric acid
  • α-D-Ribofuranose 1-(dihydrogen phosphate)
  • α-D-Ribofuranose 1-(dihydrogen phosphoric acid)
  • α-D-Ribofuranose 1-phosphate
  • α-D-Ribofuranose 1-phosphoric acid
  • α-D-Ribose 1-phosphate
  • α-D-Ribose 1-phosphoric acid
  • α-D-Ribose-1P
Chemical Formula: C5H11O8P
Average Molecular Weight: 230.1098
Monoisotopic Molecular Weight: 230.01915384
InChI Key: YXJDFQJKERBOBM-TXICZTDVSA-N
InChI:InChI=1S/C5H11O8P/c6-1-2-3(7)4(8)5(12-2)13-14(9,10)11/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1
CAS number: 14075-00-4
IUPAC Name:{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name: ribose 1-phosphate
SMILES:OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
Kingdom Organic compounds
Super ClassOrganophosphorus compounds
Class Organic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct Parent Monoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Organic phosphate
  • Monosaccharide
  • Saccharide
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
LogP:-2.919PhysProp
Predicted Properties
PropertyValueSource
Water Solubility35.2 mg/mLALOGPS
logP-2ALOGPS
logP-2.4ChemAxon
logS-0.82ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity40.83 m3·mol-1ChemAxon
Polarizability18.17 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Guanosine + Phosphate <> Guanine + Ribose-1-phosphate
Inosine + Phosphate <> Hypoxanthine + Ribose-1-phosphate
Ribose-1-phosphate <> D-Ribose-5-phosphate
Phosphate + Xanthosine <> Ribose-1-phosphate + Xanthine
Phosphate + Uridine <> Ribose-1-phosphate + Uracil
Adenosine + Phosphate <> Adenine + Ribose-1-phosphate
alpha-D-Ribose 1-phosphate + Ribose-1-phosphate <> D-Ribose-5-phosphate
Uridine + Phosphate <> Uracil + alpha-D-Ribose 1-phosphate + Ribose-1-phosphate
Ribose-1-phosphate + Adenosine triphosphate > Hydrogen ion + Ribose 1,5-bisphosphate + ADP
a purine ribonucleoside + Phosphate <> a purine base + Ribose-1-phosphate
Purine nucleoside + Inorganic phosphate > Purine + Ribose-1-phosphate
Uridine + Inorganic phosphate > Uracil + Ribose-1-phosphate
Purine nucleoside + Phosphate + Purine deoxyribonucleoside <> Purine + Ribose-1-phosphate + Deoxyribose 1-phosphate
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9230000000-bf825c0a48e8f3fb1db5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9330000000-af34500034734754addaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-ea509fab4675ba638745View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9180000000-4449ca89ca00716d8cefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-c74e6f3e6a87ec4b57fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-81a191a3e73e8031cb23View in MoNA
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Giorgelli, F., Bottai, C., Mascia, L., Scolozzi, C., Camici, M., Ipata, P. L. (1997). "Recycling of alpha-D-ribose 1-phosphate for nucleoside interconversion." Biochim Biophys Acta 1335:6-22. Pubmed: 9133638
  • 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
  • Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Tochikura, Tatsurokuro; Sakai, Takuo; Ogata, Koichi. Ribose 1-phosphate production by fermentation. Jpn. Tokkyo Koho (1969), 3 pp.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16300
HMDB IDHMDB01489
Pubchem Compound ID123732
Kegg IDC00620
ChemSpider ID388373
Wikipedia IDNot Available
BioCyc IDRIBOSE-1P
EcoCyc IDRIBOSE-1P
Ligand ExpoRDP

Enzymes

Protein Details
• 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
Locus Tag:
PA5131
Molecular weight:
55.6 kDa
Reactions
Alpha-D-glucose 1-phosphate = alpha-D-glucose 6-phosphate.