<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-05-31 14:37:05 -0600</creation_date>
  <update_date>2015-06-03 17:19:42 -0600</update_date>
  <accession>ECMDB20282</accession>
  <m2m_id>M2MDB001122</m2m_id>
  <name>L-Ribose</name>
  <description>Ribose is an organic compound that occurs widely in nature. It is an aldopentose, a monosaccharide containing five carbon atoms that in its acyclic form has an aldehyde functional group at one end. Typically, ribose exists in the cyclic form. It comprises the backbone of RNA, a biopolymer that is the basis of genetic transcription. It is related to deoxyribose, as found in DNA, by the removal of one hydroxy group. Once phosphorylated, ribose can become a subunit of ATP, NADH, and several other compounds that are critical to metabolism.  Ribose exists in two enantiomeric forms, primarily as D-ribose. L-ribose is the synthetic mirror image of D-ribose. (Wikipedia)  In E. coli, L-ribose can act as an competitive inhibitor of glucose dehydrogenase. (EcoCyc)</description>
  <synonyms>
    <synonym>(2S,3S,4S)-2,3,4,5-tetrahydroxypentanal</synonym>
    <synonym>Aldehydo-L-ribo-pentose</synonym>
    <synonym>Aldehydo-L-ribose</synonym>
    <synonym>Arabinose</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>(2S,3S,4S)-2,3,4,5-tetrahydroxypentanal</iupac_name>
  <traditional_iupac>L-ribose</traditional_iupac>
  <cas_registry_number>24259-59-4</cas_registry_number>
  <smiles>[H][C@](O)(CO)[C@]([H])(O)[C@]([H])(O)C=O</smiles>
  <inchi>InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5-/m1/s1</inchi>
  <inchikey>PYMYPHUHKUWMLA-MROZADKFSA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
    <cellular_location>Cytoplasm</cellular_location>
    <cellular_location>Periplasm</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.80e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value> 99 °C, 372 K, 210 °F</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>11.87</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2S,3S,4S)-2,3,4,5-tetrahydroxypentanal</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>[H][C@](O)(CO)[C@]([H])(O)[C@]([H])(O)C=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C5H10O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>PYMYPHUHKUWMLA-MROZADKFSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>97.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>31.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>13.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</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>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1085261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>326241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33121</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id></hmdb_id>
  <pubchem_compound_id>90428</pubchem_compound_id>
  <chemspider_id>81643</chemspider_id>
  <kegg_id></kegg_id>
  <chebi_id>46997</chebi_id>
  <biocyc_id>CPD-6001</biocyc_id>
  <het_id/>
  <wikipidia></wikipidia>
  <foodb_id></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>
  </general_references>
  <synthesis_reference></synthesis_reference>
  <msds_url/>
  <enzymes>
    <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>
  </enzymes>
  <transporters>
    <enzyme>
      <name>Sugar efflux transporter C</name>
      <uniprot_id>P31436</uniprot_id>
      <uniprot_name>SETC_ECOLI</uniprot_name>
      <gene_name>setC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P31436.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>
  </transporters>
  <reactions>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
