<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-05-31 10:25:29 -0600</creation_date>
  <update_date>2015-09-13 15:15:18 -0600</update_date>
  <accession>ECMDB00283</accession>
  <m2m_id>M2MDB000116</m2m_id>
  <name>Ribose</name>
  <description>Ribose is a pentose that is actively used in many biological systems usually in its D-form. Ribose constitutes the backbone of RNA, a biopolymer that is the basis of genetic transcription. It is related to deoxyribose, as found in DNA. Once phosphorylated, ribose can become a subunit of ATP, NADH, and several other compounds that are critical to metabolism like the secondary messengers cAMP and cGMP. In cells D-ribose must be phosphorylated before it can be used. Ribokinase catalyzes this reaction by converting D-ribose to D-ribose 5-phosphate. </description>
  <synonyms>
    <synonym>5-Methylthio-D-ribose</synonym>
    <synonym>5-Methylthioribose</synonym>
    <synonym>a-D-Ribose</synonym>
    <synonym>a-D-Ribose-5</synonym>
    <synonym>a-delta-Ribose</synonym>
    <synonym>a-delta-Ribose-5</synonym>
    <synonym>a-δ-Ribose</synonym>
    <synonym>a-δ-Ribose-5</synonym>
    <synonym>Alpha-D-Ribose</synonym>
    <synonym>Alpha-D-Ribose-5</synonym>
    <synonym>Alpha-delta-Ribose</synonym>
    <synonym>Alpha-delta-Ribose-5</synonym>
    <synonym>D-(-)-Ribose</synonym>
    <synonym>D-Ribo-2,3,4,5-tetrahydroxyvaleraldehyde</synonym>
    <synonym>D-Ribose</synonym>
    <synonym>Delta-(-)-Ribose</synonym>
    <synonym>Delta-Ribo-2,3,4,5-tetrahydroxyvaleraldehyde</synonym>
    <synonym>Delta-Ribose</synonym>
    <synonym>MTR</synonym>
    <synonym>Pentose</synonym>
    <synonym>Ribose</synonym>
    <synonym>S-Methyl-5-thio-D-ribofuranose</synonym>
    <synonym>α-D-Ribose</synonym>
    <synonym>α-D-Ribose-5</synonym>
    <synonym>α-δ-Ribose</synonym>
    <synonym>α-δ-Ribose-5</synonym>
    <synonym>δ-(-)-Ribose</synonym>
    <synonym>δ-ribo-2,3,4,5-Tetrahydroxyvaleraldehyde</synonym>
    <synonym>δ-Ribose</synonym>
  </synonyms>
  <chemical_formula>C5H10O5</chemical_formula>
  <average_molecular_weight>150.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>150.05282343</monisotopic_moleculate_weight>
  <iupac_name>(3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol</iupac_name>
  <traditional_iupac>D-ribofuranoside</traditional_iupac>
  <cas_registry_number>50-69-1</cas_registry_number>
  <smiles>OC[C@H]1OC(O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5?/m1/s1</inchi>
  <inchikey>HMFHBZSHGGEWLO-SOOFDHNKSA-N</inchikey>
  <state></state>
  <cellular_locations>
    <cellular_location>Cytosol</cellular_location>
    <cellular_location>Extra-organism</cellular_location>
    <cellular_location>Periplasm</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.07e+03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>11.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>150.1299</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>150.05282343</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC[C@H]1OC(O)[C@H](O)[C@@H]1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C5H10O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5?/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>HMFHBZSHGGEWLO-SOOFDHNKSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>90.15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>29.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>13.68</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
    <pathway>
      <name>Pentose phosphate pathway</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00030</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Purine metabolism</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00230</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Pyrimidine metabolism</name>
      <description>The metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate.
Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate.
        1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
        2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
        3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate
        4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate    The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
        5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
        6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.

The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate.</description>
      <pathwhiz_id>PW000942</pathwhiz_id>
      <kegg_map_id>ec00240</kegg_map_id>
      <subject>Metabolic</subject>
    </pathway>
    <pathway>
      <name>ABC transporters</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec02010</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Bacterial chemotaxis</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec02030</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Metabolic pathways</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>eco01100</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Ribose Degradation</name>
      <description>D-ribose, which can serve as a total source of carbon and energy for E. coli, enters the cell via a high-affinity ABC transport system and hence in unphosphorylated form. The crystal structure of the periplasmic ribose binding protein of the ribose ABC transporter showed it to bind (and thus presumably to facilitate transport of) β-D-ribopyranose. ribose pyranase accelerates the conversion between the pyranose and furanose forms of β-D-ribose. Interconversion of the α- and β-anomers of D-ribofuranose is fast and spontaneous. ribokinase then converts it to D-ribose 5-phosphate, an intermediate of the pentose phosphate pathway, and hence it flows through the pathways of central metabolism to satisfy the cell's need for precursor metabolites, reducing power, and metabolic energy. (EcoCyc)</description>
      <pathwhiz_id>PW002102</pathwhiz_id>
      <kegg_map_id/>
      <subject>Metabolic</subject>
    </pathway>
    <pathway>
      <name>&lt;i&gt;S&lt;/i&gt;-methyl-5'-thioadenosine degradation IV</name>
      <ecocyc_pathway_id>PWY0-1391</ecocyc_pathway_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>168746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1056715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1056717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1056719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1056721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>143309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2236312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2237049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2238484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2239120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2240571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2241111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2242643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2243233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2251535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2362058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2362059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2362060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2599739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2599740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2599741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1254</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB00283</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id>5575</chemspider_id>
  <kegg_id>C00121</kegg_id>
  <chebi_id/>
  <biocyc_id></biocyc_id>
  <het_id/>
  <wikipidia>Ribose</wikipidia>
  <foodb_id/>
  <general_references>
    <reference>
      <reference_text>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.</reference_text>
      <pubmed_id>21097882</pubmed_id>
    </reference>
    <reference>
      <reference_text>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.</reference_text>
      <pubmed_id>22080510</pubmed_id>
    </reference>
    <reference>
      <reference_text>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.</reference_text>
      <pubmed_id>17765195</pubmed_id>
    </reference>
    <reference>
      <reference_text>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.</reference_text>
      <pubmed_id>18331064</pubmed_id>
    </reference>
    <reference>
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    <reference>
      <reference_text>Boros LG, Steinkamp MP, Fleming JC, Lee WN, Cascante M, Neufeld EJ: Defective RNA ribose synthesis in fibroblasts from patients with thiamine-responsive megaloblastic anemia (TRMA). Blood. 2003 Nov 15;102(10):3556-61. Epub 2003 Jul 31.</reference_text>
      <pubmed_id>12893755</pubmed_id>
    </reference>
    <reference>
      <reference_text>Takeda Y, Usukura M, Yoneda T, Oda N, Ito Y, Mabuchi H: The expression of messenger RNA for ADP-ribosyl cyclase in aldosterone-producing adenomas. Clin Endocrinol (Oxf). 2005 Apr;62(4):504-8.</reference_text>
      <pubmed_id>15807884</pubmed_id>
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    <reference>
      <reference_text>Thomas D, Yang H, Boffa DJ, Ding R, Sharma VK, Lagman M, Li B, Hering B, Mohanakumar T, Lakey J, Kapur S, Hancock WW, Suthanthiran M: Proapoptotic Bax is hyperexpressed in isolated human islets compared with antiapoptotic Bcl-2. Transplantation. 2002 Dec 15;74(11):1489-96.</reference_text>
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      <pubmed_id>17618002</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference>Park, Yong-Cheol; Choi, Jin-Ho; Bennett, George N.; Seo, Jin-Ho. Characterization of D-ribose biosynthesis in Bacillus subtilis JY200 deficient in transketolase gene. Journal of Biotechnology  (2006),  121(4),  508-516. </synthesis_reference>
  <msds_url>http://hmdb.ca/system/metabolites/msds/000/000/205/original/HMDB00283.pdf?1358894050</msds_url>
  <enzymes>
    <enzyme>
      <name>Ribose import ATP-binding protein RbsA</name>
      <uniprot_id>P04983</uniprot_id>
      <uniprot_name>RBSA_ECOLI</uniprot_name>
      <gene_name>rbsA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P04983.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Ribokinase</name>
      <uniprot_id>P0A9J6</uniprot_id>
      <uniprot_name>RBSK_ECOLI</uniprot_name>
      <gene_name>rbsK</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0A9J6.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Class B acid phosphatase</name>
      <uniprot_id>P0AE22</uniprot_id>
      <uniprot_name>APHA_ECOLI</uniprot_name>
      <gene_name>aphA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AE22.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Non-specific ribonucleoside hydrolase rihC</name>
      <uniprot_id>P22564</uniprot_id>
      <uniprot_name>RIHC_ECOLI</uniprot_name>
      <gene_name>rihC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P22564.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>D-allose import ATP-binding protein AlsA</name>
      <uniprot_id>P32721</uniprot_id>
      <uniprot_name>ALSA_ECOLI</uniprot_name>
      <gene_name>alsA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P32721.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Pyrimidine-specific ribonucleoside hydrolase rihB</name>
      <uniprot_id>P33022</uniprot_id>
      <uniprot_name>RIHB_ECOLI</uniprot_name>
      <gene_name>rihB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P33022.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Sugar phosphatase supH</name>
      <uniprot_id>P75792</uniprot_id>
      <uniprot_name>SUPH_ECOLI</uniprot_name>
      <gene_name>supH</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P75792.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Uncharacterized ABC transporter ATP-binding protein ytfR</name>
      <uniprot_id>Q6BEX0</uniprot_id>
      <uniprot_name>YTFR_ECOLI</uniprot_name>
      <gene_name>ytfR</gene_name>
      <protein_url>http://ecmdb.ca/proteins/Q6BEX0.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Inner membrane ABC transporter permease protein yjfF</name>
      <uniprot_id>P37772</uniprot_id>
      <uniprot_name>YJFF_ECOLI</uniprot_name>
      <gene_name>yjfF</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P37772.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>ABC transporter periplasmic-binding protein ytfQ</name>
      <uniprot_id>P39325</uniprot_id>
      <uniprot_name>YTFQ_ECOLI</uniprot_name>
      <gene_name>ytfQ</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P39325.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Inner membrane ABC transporter permease protein ytfT</name>
      <uniprot_id>P39328</uniprot_id>
      <uniprot_name>YTFT_ECOLI</uniprot_name>
      <gene_name>ytfT</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P39328.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Ribose transport system permease protein rbsC</name>
      <uniprot_id>P0AGI1</uniprot_id>
      <uniprot_name>RBSC_ECOLI</uniprot_name>
      <gene_name>rbsC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AGI1.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>D-allose transport system permease protein AlsC</name>
      <uniprot_id>P32720</uniprot_id>
      <uniprot_name>ALSC_ECOLI</uniprot_name>
      <gene_name>alsC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P32720.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>D-ribose pyranase</name>
      <uniprot_id>P04982</uniprot_id>
      <uniprot_name>RBSD_ECOLI</uniprot_name>
      <gene_name>rbsD</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P04982.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Pyrimidine-specific ribonucleoside hydrolase rihA</name>
      <uniprot_id>P41409</uniprot_id>
      <uniprot_name>RIHA_ECOLI</uniprot_name>
      <gene_name>rihA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P41409.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>D-allose-binding periplasmic protein</name>
      <uniprot_id>P39265</uniprot_id>
      <uniprot_name>ALSB_ECOLI</uniprot_name>
      <gene_name>alsB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P39265.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>D-ribose-binding periplasmic protein</name>
      <uniprot_id>P02925</uniprot_id>
      <uniprot_name>RBSB_ECOLI</uniprot_name>
      <gene_name>rbsB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02925.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
    <enzyme>
      <name>Ribose import ATP-binding protein RbsA</name>
      <uniprot_id>P04983</uniprot_id>
      <uniprot_name>RBSA_ECOLI</uniprot_name>
      <gene_name>rbsA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P04983.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>D-allose import ATP-binding protein AlsA</name>
      <uniprot_id>P32721</uniprot_id>
      <uniprot_name>ALSA_ECOLI</uniprot_name>
      <gene_name>alsA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P32721.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Uncharacterized ABC transporter ATP-binding protein ytfR</name>
      <uniprot_id>Q6BEX0</uniprot_id>
      <uniprot_name>YTFR_ECOLI</uniprot_name>
      <gene_name>ytfR</gene_name>
      <protein_url>http://ecmdb.ca/proteins/Q6BEX0.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Inner membrane ABC transporter permease protein yjfF</name>
      <uniprot_id>P37772</uniprot_id>
      <uniprot_name>YJFF_ECOLI</uniprot_name>
      <gene_name>yjfF</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P37772.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>ABC transporter periplasmic-binding protein ytfQ</name>
      <uniprot_id>P39325</uniprot_id>
      <uniprot_name>YTFQ_ECOLI</uniprot_name>
      <gene_name>ytfQ</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P39325.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Inner membrane ABC transporter permease protein ytfT</name>
      <uniprot_id>P39328</uniprot_id>
      <uniprot_name>YTFT_ECOLI</uniprot_name>
      <gene_name>ytfT</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P39328.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Ribose transport system permease protein rbsC</name>
      <uniprot_id>P0AGI1</uniprot_id>
      <uniprot_name>RBSC_ECOLI</uniprot_name>
      <gene_name>rbsC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AGI1.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>D-allose transport system permease protein AlsC</name>
      <uniprot_id>P32720</uniprot_id>
      <uniprot_name>ALSC_ECOLI</uniprot_name>
      <gene_name>alsC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P32720.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>D-allose-binding periplasmic protein</name>
      <uniprot_id>P39265</uniprot_id>
      <uniprot_name>ALSB_ECOLI</uniprot_name>
      <gene_name>alsB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P39265.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Outer membrane protein N</name>
      <uniprot_id>P77747</uniprot_id>
      <uniprot_name>OMPN_ECOLI</uniprot_name>
      <gene_name>ompN</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P77747.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Outer membrane pore protein E</name>
      <uniprot_id>P02932</uniprot_id>
      <uniprot_name>PHOE_ECOLI</uniprot_name>
      <gene_name>phoE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02932.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>D-ribose-binding periplasmic protein</name>
      <uniprot_id>P02925</uniprot_id>
      <uniprot_name>RBSB_ECOLI</uniprot_name>
      <gene_name>rbsB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02925.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Outer membrane protein F</name>
      <uniprot_id>P02931</uniprot_id>
      <uniprot_name>OMPF_ECOLI</uniprot_name>
      <gene_name>ompF</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02931.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Outer membrane protein C</name>
      <uniprot_id>P06996</uniprot_id>
      <uniprot_name>OMPC_ECOLI</uniprot_name>
      <gene_name>ompC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P06996.xml</protein_url>
    </enzyme>
  </transporters>
  <reactions>
    <reaction_text>Adenosine triphosphate + Water + Ribose &gt; ADP + Hydrogen ion + Phosphate + Ribose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Water + Ribose &gt; ADP + Hydrogen ion + Phosphate + Ribose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Cytidine + Water &gt; Cytosine + Ribose</reaction_text>
    <kegg_reaction_id>R02137</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Water + Uridine &gt; Ribose + Uracil</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine + Water &gt; Adenine + Ribose</reaction_text>
    <kegg_reaction_id>R01245</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Water + Inosine &gt; Hypoxanthine + Ribose</reaction_text>
    <kegg_reaction_id>R01770</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Water + Xanthosine &gt; Ribose + Xanthine</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Water + D-Ribose-5-phosphate &gt; Phosphate + Ribose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Ribose &lt;&gt; ADP + Hydrogen ion + D-Ribose-5-phosphate</reaction_text>
    <kegg_reaction_id>R01051</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Ribose &lt;&gt; ADP + D-Ribose-5-phosphate</reaction_text>
    <kegg_reaction_id>R01051</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine + Water &lt;&gt; Adenine + Ribose</reaction_text>
    <kegg_reaction_id>R01245</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Guanosine + Water &lt;&gt; Guanine + Ribose</reaction_text>
    <kegg_reaction_id>R01677</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Inosine + Water &lt;&gt; Hypoxanthine + Ribose</reaction_text>
    <kegg_reaction_id>R01770</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Cytidine + Water &lt;&gt; Cytosine + Ribose</reaction_text>
    <kegg_reaction_id>R02137</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Ribose &gt; ADP + D-Ribose-5-phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>A pyrimidine nucleoside + Water &gt; Ribose + a pyrimidine base</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Pyrimidine nucleoside + Water &lt;&gt; Ribose + Pyrimidine</reaction_text>
    <kegg_reaction_id>R02172 </kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Ribose + Adenosine triphosphate &gt; D-Ribose-5-phosphate + ADP + Hydrogen ion</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id>PW_R006131</pw_reaction_id>
    <reaction_text>Adenosine triphosphate + Ribose &lt;&gt; ADP + Hydrogen ion + D-Ribose-5-phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Ribose &lt;&gt; ADP + Hydrogen ion + D-Ribose-5-phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
