<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-05-31 13:48:42 -0600</creation_date>
  <update_date>2015-09-13 12:56:10 -0600</update_date>
  <accession>ECMDB01266</accession>
  <m2m_id>M2MDB000316</m2m_id>
  <name>L-Sorbose</name>
  <description>Sorbose is a ketose belonging to the group of sugars known as monosaccharides. The commercial production of vitamin C (ascorbic acid) often begins with sorbose.</description>
  <synonyms>
    <synonym>a-L-Sorbopyranose</synonym>
    <synonym>Alpha-L-Sorbopyranose</synonym>
    <synonym>Hex-2-ulose</synonym>
    <synonym>L(-) Sorbose for biochemistry</synonym>
    <synonym>L(-)-Sorbose</synonym>
    <synonym>L-(-)-Sorbose</synonym>
    <synonym>L-(-)-Sorbose 99%</synonym>
    <synonym>L-1,3,4,5,6-Pentahydroxyhexan-2-one</synonym>
    <synonym>L-Sorbinose</synonym>
    <synonym>L-Sorbose</synonym>
    <synonym>L-Xylo-2-Hexulose</synonym>
    <synonym>L-Xylo-hexulose</synonym>
    <synonym>Sorbin</synonym>
    <synonym>Sorbinose</synonym>
    <synonym>Sorbose</synonym>
    <synonym>Xylo-Hexulose</synonym>
    <synonym>α-L-Sorbopyranose</synonym>
  </synonyms>
  <chemical_formula>C6H12O6</chemical_formula>
  <average_molecular_weight>180.1559</average_molecular_weight>
  <monisotopic_moleculate_weight>180.063388116</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>α-L-sorbopyranose</traditional_iupac>
  <cas_registry_number>87-79-6</cas_registry_number>
  <smiles>OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5-,6+/m0/s1</inchi>
  <inchikey>LKDRXBCSQODPBY-BGPJRJDNSA-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>-2.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.19e+03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>165 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>10.29</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>180.1559</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>180.063388116</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C6H12O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5-,6+/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>LKDRXBCSQODPBY-BGPJRJDNSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>110.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>36.36</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>16.05</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>6</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>
    <pathway>
      <name>Fructose and mannose metabolism</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00051</kegg_map_id>
      <subject/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>132258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>139992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>147069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2394217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2394218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2394219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2571473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2571474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2571475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1616</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB01266</hmdb_id>
  <pubchem_compound_id>439192</pubchem_compound_id>
  <chemspider_id>390208</chemspider_id>
  <kegg_id>C00247</kegg_id>
  <chebi_id>17266</chebi_id>
  <biocyc_id>CPD-9569</biocyc_id>
  <het_id>SOE</het_id>
  <wikipidia>L-Sorbose</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>Nakamura J, Koh N, Sakakibara F, Hamada Y, Wakao T, Sasaki H, Mori K, Nakashima E, Naruse K, Hotta N: Diabetic neuropathy in sucrose-fed Otsuka Long-Evans Tokushima fatty rats: effect of an aldose reductase inhibitor, TAT. Life Sci. 1997;60(21):1847-57.</reference_text>
      <pubmed_id>9154994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gryz EA, Galicka-Latala D, Szczudlik A, Sieradzki J: [Etiopathogenesis of diabetic neuropathy]  Przegl Lek. 2000;57(12):727-31.</reference_text>
      <pubmed_id>11398597</pubmed_id>
    </reference>
    <reference>
      <reference_text>Wang C, So SY, Wong KK, So WW, Chan SY: Chronic sinopulmonary disease in Chinese patients with obstructive azoospermia. J Androl. 1987 Jul-Aug;8(4):225-9.</reference_text>
      <pubmed_id>3624059</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kossi J, Peltonen J, Uotila P, Laato M: Differential effects of hexoses and sucrose, and platelet-derived growth factor isoforms on cyclooxygenase-1 and -2 mRNA expression in keloid, hypertrophic scar and granulation tissue fibroblasts. Arch Dermatol Res. 2001 Mar;293(3):126-32.</reference_text>
      <pubmed_id>11357226</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gross KC, Houghton MP, Senterfit LB: Presumptive speciation of Streptococcus bovis and other group D streptococci from human sources by using arginine and pyruvate tests. J Clin Microbiol. 1975 Jan;1(1):54-60.</reference_text>
      <pubmed_id>1176592</pubmed_id>
    </reference>
    <reference>
      <reference_text>Fukasawa M, Takayama E, Shinomiya N, Okumura A, Rokutanda M, Yamamoto N, Sakakibara R: Identification of the promoter region of human placental 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase gene. Biochem Biophys Res Commun. 2000 Jan 27;267(3):703-8.</reference_text>
      <pubmed_id>10673355</pubmed_id>
    </reference>
    <reference>
      <reference_text>Le KA, Tappy L: Metabolic effects of fructose.  Curr Opin Clin Nutr Metab Care. 2006 Jul;9(4):469-75.</reference_text>
      <pubmed_id>16778579</pubmed_id>
    </reference>
    <reference>
      <reference_text>Fukasawa M, Tsuchiya T, Takayama E, Shinomiya N, Uyeda K, Sakakibara R, Seki S: Identification and characterization of the hypoxia-responsive element of the human placental 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase gene. J Biochem (Tokyo). 2004 Sep;136(3):273-7.</reference_text>
      <pubmed_id>15598882</pubmed_id>
    </reference>
    <reference>
      <reference_text>Yanez AJ, Bertinat R, Spichiger C, Carcamo JG, de Los Angeles Garcia M, Concha II, Nualart F, Slebe JC: Novel expression of liver FBPase in Langerhans islets of human and rat pancreas. J Cell Physiol. 2005 Oct;205(1):19-24.</reference_text>
      <pubmed_id>15965961</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lee YH, Li Y, Uyeda K, Hasemann CA: Tissue-specific structure/function differentiation of the liver isoform of 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase. J Biol Chem. 2003 Jan 3;278(1):523-30. Epub 2002 Oct 11.</reference_text>
      <pubmed_id>12379646</pubmed_id>
    </reference>
    <reference>
      <reference_text>Minchenko O, Opentanova I, Minchenko D, Ogura T, Esumi H: Hypoxia induces transcription of 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase-4 gene via hypoxia-inducible factor-1alpha activation. FEBS Lett. 2004 Oct 8;576(1-2):14-20.</reference_text>
      <pubmed_id>15474002</pubmed_id>
    </reference>
    <reference>
      <reference_text>Andrade-Rocha FT: Physical analysis of ejaculate to evaluate the secretory activity of the seminal vesicles and prostate. Clin Chem Lab Med. 2005;43(11):1203-10.</reference_text>
      <pubmed_id>16232086</pubmed_id>
    </reference>
    <reference>
      <reference_text>Roy S, Banerjee A, Pandey HC, Singh G, Kumari GL: Application of seminal germ cell morphology and semen biochemistry in the diagnosis and management of azoospermic subjects. Asian J Androl. 2001 Mar;3(1):55-62.</reference_text>
      <pubmed_id>11250795</pubmed_id>
    </reference>
    <reference>
      <reference_text>Blakemore SJ, Aledo JC, James J, Campbell FC, Lucocq JM, Hundal HS: The GLUT5 hexose transporter is also localized to the basolateral membrane of the human jejunum. Biochem J. 1995 Jul 1;309 ( Pt 1):7-12.</reference_text>
      <pubmed_id>7619085</pubmed_id>
    </reference>
    <reference>
      <reference_text>Abou El Fadil-Nicol F, Berger F, Descroix-Vagne M, Pansu D: Presence of sorbin in human digestive tract and endocrine digestive tumours. Gut. 2000 Feb;46(2):182-90.</reference_text>
      <pubmed_id>10644311</pubmed_id>
    </reference>
    <reference>
      <reference_text>Faeh D, Minehira K, Schwarz JM, Periasamy R, Park S, Tappy L: Effect of fructose overfeeding and fish oil administration on hepatic de novo lipogenesis and insulin sensitivity in healthy men. Diabetes. 2005 Jul;54(7):1907-13.</reference_text>
      <pubmed_id>15983189</pubmed_id>
    </reference>
    <reference>
      <reference_text>Atsumi T, Chesney J, Metz C, Leng L, Donnelly S, Makita Z, Mitchell R, Bucala R: High expression of inducible 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase (iPFK-2; PFKFB3) in human cancers. Cancer Res. 2002 Oct 15;62(20):5881-7.</reference_text>
      <pubmed_id>12384552</pubmed_id>
    </reference>
    <reference>
      <reference_text>Wu LY, Juan CC, Hwang LS, Hsu YP, Ho PH, Ho LT: Green tea supplementation ameliorates insulin resistance and increases glucose transporter IV content in a fructose-fed rat model. Eur J Nutr. 2004 Apr;43(2):116-24. Epub 2004 Jan 6.</reference_text>
      <pubmed_id>15083319</pubmed_id>
    </reference>
    <reference>
      <reference_text>Ludwig M, Vidal A, Diemer T, Pabst W, Failing K, Weidner W: Seminal secretory capacity of the male accessory sex glands in chronic pelvic pain syndrome (CPPS)/chronic prostatitis with special focus on the new prostatitis classification. Eur Urol. 2002 Jul;42(1):24-8.</reference_text>
      <pubmed_id>12121725</pubmed_id>
    </reference>
    <reference>
      <reference_text>Massucco P, Mattiello L, Russo I, Traversa M, Doronzo G, Anfossi G, Trovati M: High glucose rapidly activates the nitric oxide/cyclic nucleotide pathway in human platelets via an osmotic mechanism. Thromb Haemost. 2005 Mar;93(3):517-26.</reference_text>
      <pubmed_id>15735804</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference>Banjopnoppakun, Tanaphat; Moonmangmee, Somporn; Moonmangmee, Duangtip.  Production of L-sorbose by thermotolerant acetic acid bacteria.    Proceeding of the Kasetsart University Annual Conference, 44th, Bangkok, Thailand, Jan. 30-Feb. 2, 2006  (2006),    </synthesis_reference>
  <msds_url>http://hmdb.ca/system/metabolites/msds/000/001/134/original/HMDB01266.pdf?1358461776</msds_url>
  <enzymes>
  </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>
  </transporters>
  <reactions>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
