Record Information
Version2.0
Creation Date2012-05-31 14:06:32 -0600
Update Date2015-10-02 02:25:46 -0600
Secondary Accession Numbers
  • ECMDB04147
Identification
Name:Ribose-1-phosphate
DescriptionRibose 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. (PMID: 9133638)
Structure
Thumb
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
Weight:Average: 230.1098
Monoisotopic: 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
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
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity40.83 m³·mol⁻¹ChemAxon
Polarizability18.17 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
PRPP BiosynthesisPW000909 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine ribonucleosides degradtionPW002024 ThumbThumb?image type=greyscaleThumb?image type=simple
adenine and adenosine salvage IPW002069 ThumbThumb?image type=greyscaleThumb?image type=simple
adenine and adenosine salvage IIPW002071 ThumbThumb?image type=greyscaleThumb?image type=simple
adenosine nucleotides degradationPW002091 ThumbThumb?image type=greyscaleThumb?image type=simple
guanine and guanosine salvagePW002074 ThumbThumb?image type=greyscaleThumb?image type=simple
purine ribonucleosides degradationPW002076 ThumbThumb?image type=greyscaleThumb?image type=simple
pyrimidine ribonucleosides degradationPW002104 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
1020± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
686± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
1320± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
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, Positivesplash10-0002-9110000000-add01bb15cc1fd9e2e29View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-2931000000-fe633c386d1b3ab9db9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-e2c9f6f60320b17dd479View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01t9-9250000000-029c27941ed85100b53cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-311ca08c80d0a6c765daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-36d97c26c72c69ab56c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-08796c6cb24ecefd9abfView in MoNA
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

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.
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
Gene Name:
deoD
Uniprot ID:
P0ABP8
Molecular weight:
25950
Reactions
Purine nucleoside + phosphate = purine + alpha-D-ribose 1-phosphate.
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1- phosphate. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis
Gene Name:
udp
Uniprot ID:
P12758
Molecular weight:
27159
Reactions
Uridine + phosphate = uracil + alpha-D-ribose 1-phosphate.
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.
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the nucleoside molecule, with the formation of the corresponding free bases and pentose-1-phosphate. This protein can degrade all purine nucleosides except adenosine and deoxyadenosine
Gene Name:
xapA
Uniprot ID:
P45563
Molecular weight:
29834
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
yhfW
Uniprot ID:
P45549
Molecular weight:
44559