<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-05-31 13:44:38 -0600</creation_date>
  <update_date>2015-06-03 15:53:42 -0600</update_date>
  <accession>ECMDB01076</accession>
  <m2m_id>M2MDB000243</m2m_id>
  <name>Fructose 1-phosphate</name>
  <description>Fructose 1-phosphate is an intermediate metabolite in the Fructose and mannose metabolism pathway.  It is generated by fructokinase and it is broken down by aldolase B into glyceraldehyde and dihydroxyacetone phosphate (DHAP).</description>
  <synonyms>
    <synonym>&amp;beta;-D-fructose-1-P</synonym>
    <synonym>&amp;beta;-D-fructose-1-phosphate</synonym>
    <synonym>&amp;beta;-D-fructose-1-phosphoric acid</synonym>
    <synonym>b-D-Fructose-1-P</synonym>
    <synonym>b-D-Fructose-1-phosphate</synonym>
    <synonym>b-D-Fructose-1-phosphoric acid</synonym>
    <synonym>Beta-D-Fructose-1-P</synonym>
    <synonym>Beta-D-Fructose-1-phosphate</synonym>
    <synonym>beta-D-Fructose-1-phosphoric acid</synonym>
    <synonym>D-Fructose 1-phosphate</synonym>
    <synonym>D-Fructose 1-phosphoric acid</synonym>
    <synonym>D-Fructose-1-P</synonym>
    <synonym>D-Fructose-1-phosphate</synonym>
    <synonym>D-Fructose-1-phosphoric acid</synonym>
    <synonym>Fructose 1-phosphate</synonym>
    <synonym>Fructose 1-phosphoric acid</synonym>
    <synonym>Fructose-1-P</synonym>
    <synonym>Fructose-1-phosphate</synonym>
    <synonym>Fructose-1-phosphoric acid</synonym>
    <synonym>Fructose1P</synonym>
    <synonym>β-D-Fructose-1-P</synonym>
    <synonym>β-D-Fructose-1-phosphate</synonym>
    <synonym>β-D-Fructose-1-phosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C6H13O9P</chemical_formula>
  <average_molecular_weight>260.1358</average_molecular_weight>
  <monisotopic_moleculate_weight>260.029718526</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxyphosphonic acid</traditional_iupac>
  <cas_registry_number>15978-08-2</cas_registry_number>
  <smiles>OC[C@H]1O[C@](O)(COP(O)(O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H13O9P/c7-1-3-4(8)5(9)6(10,15-3)2-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1</inchi>
  <inchikey>RHKKZBWRNHGJEZ-ARQDHWQXSA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
    <cellular_location>Cytosol</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.34e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.16</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,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>260.1358</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>260.029718526</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC[C@H]1O[C@](O)(COP(O)(O)=O)[C@@H](O)[C@@H]1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C6H13O9P</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C6H13O9P/c7-1-3-4(8)5(9)6(10,15-3)2-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>RHKKZBWRNHGJEZ-ARQDHWQXSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>156.91</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>47.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>21.06</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
    <pathway>
      <name>Fructose and mannose metabolism</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00051</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Phosphotransferase system (PTS)</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec02060</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>fructose degradation</name>
      <ecocyc_pathway_id>PWY0-1314</ecocyc_pathway_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>136551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>144285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2261767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2261768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2261769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3077712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3077713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3077714</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB01076</hmdb_id>
  <pubchem_compound_id>439394</pubchem_compound_id>
  <chemspider_id>8575807</chemspider_id>
  <kegg_id>C01094</kegg_id>
  <chebi_id>18105</chebi_id>
  <biocyc_id>FRU1P</biocyc_id>
  <het_id>F1X</het_id>
  <wikipidia>Fructose 1-phosphate</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>
      <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>
      <pubmed_id>19212411</pubmed_id>
    </reference>
    <reference>
      <reference_text>Alvarez E, Roncero I, Chowen JA, Vazquez P, Blazquez E: Evidence that glucokinase regulatory protein is expressed and interacts with glucokinase in rat brain. J Neurochem. 2002 Jan;80(1):45-53.</reference_text>
      <pubmed_id>11796742</pubmed_id>
    </reference>
    <reference>
      <reference_text>Malaisse WJ: [Metabolic interactions between glucose and fructose]  Bull Mem Acad R Med Belg. 2002;157(7-9):349-52; discussion 352-3.</reference_text>
      <pubmed_id>12647375</pubmed_id>
    </reference>
    <reference>
      <reference_text>Watford M: Small amounts of dietary fructose dramatically increase hepatic glucose uptake through a novel mechanism of glucokinase activation. Nutr Rev. 2002 Aug;60(8):253-7.</reference_text>
      <pubmed_id>12199300</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference>Hara, Yoshito.  Ion exchange separation of fructose 1-phosphate by using borate as the eluant.    Journal of Biochemistry (Tokyo, Japan)  (1959),  46  571-3.</synthesis_reference>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>Phosphoenolpyruvate-protein phosphotransferase</name>
      <uniprot_id>P08839</uniprot_id>
      <uniprot_name>PT1_ECOLI</uniprot_name>
      <gene_name>ptsI</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P08839.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Fructose-bisphosphate aldolase class 1</name>
      <uniprot_id>P0A991</uniprot_id>
      <uniprot_name>ALF1_ECOLI</uniprot_name>
      <gene_name>fbaB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0A991.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Fructose-bisphosphate aldolase class 2</name>
      <uniprot_id>P0AB71</uniprot_id>
      <uniprot_name>ALF_ECOLI</uniprot_name>
      <gene_name>fbaA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AB71.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>1-phosphofructokinase</name>
      <uniprot_id>P0AEW9</uniprot_id>
      <uniprot_name>K1PF_ECOLI</uniprot_name>
      <gene_name>fruK</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AEW9.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>PTS system fructose-specific EIIBC component</name>
      <uniprot_id>P20966</uniprot_id>
      <uniprot_name>PTFBC_ECOLI</uniprot_name>
      <gene_name>fruA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P20966.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Multiphosphoryl transfer protein</name>
      <uniprot_id>P69811</uniprot_id>
      <uniprot_name>PTFAH_ECOLI</uniprot_name>
      <gene_name>fruB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P69811.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Phosphatase yqaB</name>
      <uniprot_id>P77475</uniprot_id>
      <uniprot_name>YQAB_ECOLI</uniprot_name>
      <gene_name>yqaB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P77475.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Phosphocarrier protein HPr</name>
      <uniprot_id>P0AA04</uniprot_id>
      <uniprot_name>PTHP_ECOLI</uniprot_name>
      <gene_name>ptsH</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AA04.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
    <enzyme>
      <name>PTS system fructose-specific EIIBC component</name>
      <uniprot_id>P20966</uniprot_id>
      <uniprot_name>PTFBC_ECOLI</uniprot_name>
      <gene_name>fruA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P20966.xml</protein_url>
    </enzyme>
  </transporters>
  <reactions>
    <reaction_text>Phosphoenolpyruvic acid + D-Fructose &gt; Fructose 1-phosphate + Pyruvic acid</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Fructose 1-phosphate &gt; ADP + Fructose 1,6-bisphosphate + Hydrogen ion</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>1PFRUCTPHOSN-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Fructose 1-phosphate &lt;&gt; ADP + beta-D-Fructose 1,6-bisphosphate</reaction_text>
    <kegg_reaction_id>R02071</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Fructose 1-phosphate &lt;&gt; Dihydroxyacetone phosphate + D-Glyceraldehyde</reaction_text>
    <kegg_reaction_id>R02568</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Protein N(pi)-phospho-L-histidine + D-Fructose &lt;&gt; Protein histidine + Fructose 1-phosphate</reaction_text>
    <kegg_reaction_id>R03232</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Fructose 1-phosphate + Water &gt; D-fructose + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>RXN0-5186</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>D-fructose + Phosphoenolpyruvic acid &gt; Fructose 1-phosphate + Pyruvic acid</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>TRANS-RXN-158</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Fructose 1-phosphate &gt; ADP + Fructose 1,6-bisphosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Fructose 1-phosphate &lt;&gt; ADP + beta-D-Fructose 1,6-bisphosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
