<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-08-09 09:16:11 -0600</creation_date>
  <update_date>2015-09-13 12:56:16 -0600</update_date>
  <accession>ECMDB21421</accession>
  <m2m_id>M2MDB001816</m2m_id>
  <name>Ribitol</name>
  <description>Ribitol is a sugar alcohol with a 5-carbon chain that has a hydroxyl (OH group) attached to every carbon.   Ribitol is found in the cell wall of Gram-positive bacteria, and forms part of the structure of riboflavin and flavin mononucleotide (FMN). (Wikipedia)   In E. coli, ribitol (or more specifically D-ribitol) can act as an inhibitor of both L-arabinose isomerase and D-arabinose isomerase. (EcoCyc)</description>
  <synonyms>
    <synonym>1,2,3,4,5-pentanepentol</synonym>
    <synonym>&lt;i&gt;meso&lt;/i&gt;-ribitol</synonym>
    <synonym>Adonit</synonym>
    <synonym>Adonite</synonym>
    <synonym>Adonitol</synonym>
    <synonym>D-adonitol</synonym>
    <synonym>D-Ribitol</synonym>
    <synonym>Meso-ribitol</synonym>
    <synonym>Pentitol</synonym>
    <synonym>Ribitol</synonym>
  </synonyms>
  <chemical_formula>C5H12O5</chemical_formula>
  <average_molecular_weight>152.1458</average_molecular_weight>
  <monisotopic_moleculate_weight>152.068473494</monisotopic_moleculate_weight>
  <iupac_name>(2R,3s,4S)-pentane-1,2,3,4,5-pentol</iupac_name>
  <traditional_iupac>ribitol</traditional_iupac>
  <cas_registry_number>488-81-3</cas_registry_number>
  <smiles>OC[C@H](O)[C@H](O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-</inchi>
  <inchikey>HEBKCHPVOIAQTA-ZXFHETKHSA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.64e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>102-105 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-3.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>12.76</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2R,3s,4S)-pentane-1,2,3,4,5-pentol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>152.1458</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>152.068473494</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC[C@H](O)[C@H](O)[C@H](O)CO</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C5H12O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>HEBKCHPVOIAQTA-ZXFHETKHSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>101.15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>32.44</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>14.38</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>5</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>565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>132434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>140168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>6981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>166665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>166666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2261011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2261012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1343</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB00508</hmdb_id>
  <pubchem_compound_id>827</pubchem_compound_id>
  <chemspider_id>10254628</chemspider_id>
  <kegg_id>C00474</kegg_id>
  <chebi_id>15963</chebi_id>
  <biocyc_id>RIBITOL</biocyc_id>
  <het_id>RB0</het_id>
  <wikipidia>Ribitol</wikipidia>
  <foodb_id></foodb_id>
  <general_references>
    <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>Huck, J. H., Roos, B., Jakobs, C., van der Knaap, M. S., Verhoeven, N. M. (2004). "Evaluation of pentitol metabolism in mammalian tissues provides new insight into disorders of human sugar metabolism." Mol Genet Metab 82:231-237.</reference_text>
      <pubmed_id>15234337</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.</reference_text>
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      <pubmed_id>6434200</pubmed_id>
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      <pubmed_id>7710082</pubmed_id>
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      <pubmed_id>16435188</pubmed_id>
    </reference>
    <reference>
      <reference_text>Georgescu C, Boboc F, Dumitrescu MR, Potcoava R, Florescu PD, Racovita D: [Identification of some atypical (morpho-cultural and enzymatic) characteristics of E. coli strains isolated in different clinical and epidemiological conditions] Rev Ig Bacteriol Virusol Parazitol Epidemiol Pneumoftiziol Bacteriol       Virusol Parazitol Epidemiol. 1980 Jan-Mar;25(1):17-26.</reference_text>
      <pubmed_id>6990452</pubmed_id>
    </reference>
    <reference>
      <reference_text>Malnick H: Anaerobiospirillum thomasii sp. nov., an anaerobic spiral bacterium isolated from the feces of cats and dogs and from diarrheal feces of humans, and emendation of the genus Anaerobiospirillum. Int J Syst Bacteriol. 1997 Apr;47(2):381-4.</reference_text>
      <pubmed_id>9103625</pubmed_id>
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    <reference>
      <reference_text>Brenner DJ, Davis BR, Steigerwalt AG, Riddle CF, McWhorter AC, Allen SD, Farmer JJ 3rd, Saitoh Y, Fanning GR: Atypical biogroups of Escherichia coli found in clinical specimens and description of Escherichia hermannii sp. nov. J Clin Microbiol. 1982 Apr;15(4):703-13.</reference_text>
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    <reference>
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    <reference>
      <reference_text>Hickman-Brenner FW, Vohra MP, Huntley-Carter GP, Fanning GR, Lowery VA 3rd, Brenner DJ, Farmer JJ 3rd: Leminorella, a new genus of Enterobacteriaceae: identification of Leminorella grimontii sp. nov. and Leminorella richardii sp. nov. found in clinical specimens. J Clin Microbiol. 1985 Feb;21(2):234-9.</reference_text>
      <pubmed_id>3972991</pubmed_id>
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    <reference>
      <reference_text>Hickman-Brenner FW, Fanning GR, Arduino MJ, Brenner DJ, Farmer JJ 3rd: Aeromonas schubertii, a new mannitol-negative species found in human clinical specimens. J Clin Microbiol. 1988 Aug;26(8):1561-4.</reference_text>
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    <reference>
      <reference_text>Konishi K, Yamagishi T, Sakamoto K: A Halophilic vibrio isolated from a case of chronic cholecystitis.  Microbiol Immunol. 1981;25(12):1221-8.</reference_text>
      <pubmed_id>7334940</pubmed_id>
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      <reference_text>Brenner DJ, McWhorter AC, Kai A, Steigerwalt AG, Farmer JJ 3rd: Enterobacter asburiae sp. nov., a new species found in clinical specimens, and reassignment of Erwinia dissolvens and Erwinia nimipressuralis to the genus Enterobacter as Enterobacter dissolvens comb. nov. and Enterobacter nimipressuralis comb. nov. J Clin Microbiol. 1986 Jun;23(6):1114-20.</reference_text>
      <pubmed_id>3711302</pubmed_id>
    </reference>
    <reference>
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      <pubmed_id>3221093</pubmed_id>
    </reference>
    <reference>
      <reference_text>McWhorter AC, Haddock RL, Nocon FA, Steigerwalt AG, Brenner DJ, Aleksic S, Bockemuhl J, Farmer JJ 3rd: Trabulsiella guamensis, a new genus and species of the family Enterobacteriaceae that resembles Salmonella subgroups 4 and 5. J Clin Microbiol. 1991 Jul;29(7):1480-5.</reference_text>
      <pubmed_id>1885744</pubmed_id>
    </reference>
    <reference>
      <reference_text>Podschun R: Phenotypic properties of Klebsiella pneumoniae and K. oxytoca isolated from different sources. Zentralbl Hyg Umweltmed. 1990 May;189(6):527-35.</reference_text>
      <pubmed_id>2200423</pubmed_id>
    </reference>
    <reference>
      <reference_text>Yoshioka S, Kameyama K, Sanaka M, Sekine I, Kagimoto S, Fujitsuka S, Saitoh S: Effect of diabetes on the free polyol pattern in cataractous lenses.  Clin Chem. 1991 May;37(5):686-9.</reference_text>
      <pubmed_id>2032321</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hudson MJ, Hollis DG, Weaver RE, Galvis CG: Relationship of CDC group EO-2 and psychrobacter immobilis.  J Clin Microbiol. 1987 Oct;25(10):1907-10.</reference_text>
      <pubmed_id>3667912</pubmed_id>
    </reference>
    <reference>
      <reference_text>Brisse S, van Himbergen T, Kusters K, Verhoef J: Development of a rapid identification method for Klebsiella pneumoniae phylogenetic groups and analysis of 420 clinical isolates. Clin Microbiol Infect. 2004 Oct;10(10):942-5.</reference_text>
      <pubmed_id>15373895</pubmed_id>
    </reference>
    <reference>
      <reference_text>Roboz J, Kappatos DC, Holland JF: Role of individual serum pentitol concentrations in the diagnosis of disseminated visceral candidiasis. Eur J Clin Microbiol. 1987 Dec;6(6):708-14.</reference_text>
      <pubmed_id>3440465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Thaller MC, Berlutti F, Dainelli B, Pezzi R: New plate medium for screening and presumptive identification of gram-negative urinary tract pathogens. J Clin Microbiol. 1988 Apr;26(4):791-3.</reference_text>
      <pubmed_id>3366875</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference></synthesis_reference>
  <msds_url>http://hmdb.ca/system/metabolites/msds/000/000/427/original/HMDB00508.pdf?1358461947</msds_url>
  <enzymes>
    <enzyme>
      <name>Beta-glucuronidase</name>
      <uniprot_id>P05804</uniprot_id>
      <uniprot_name>BGLR_ECOLI</uniprot_name>
      <gene_name>uidA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P05804.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
  </transporters>
  <reactions>
    <reaction_text>Bilirubin diglucuronide + Water &gt; D-Glucuronic acid + Ribitol + Ribitol</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id>PW_R003834</pw_reaction_id>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
