<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-05-31 09:57:31 -0600</creation_date>
  <update_date>2015-09-13 12:56:06 -0600</update_date>
  <accession>ECMDB00108</accession>
  <m2m_id>M2MDB000041</m2m_id>
  <name>Ethanol</name>
  <description>Ethanol is a clear, colorless liquid.  Many bacteria species, including gut microflora such as E. coli, produce ethanol through fermentation in glucose metabolism. (HMDB, KEGG)</description>
  <synonyms>
    <synonym>1-Hydroxyethane</synonym>
    <synonym>Absolute alcohol</synonym>
    <synonym>Absolute ethanol</synonym>
    <synonym>Absolute ethyl alcohol</synonym>
    <synonym>Aethanol</synonym>
    <synonym>Aethylalkohol</synonym>
    <synonym>Alcare Hand Degermer</synonym>
    <synonym>Alcohol</synonym>
    <synonym>Alcohols</synonym>
    <synonym>Alcool ethylique</synonym>
    <synonym>Alcool etilico</synonym>
    <synonym>Algrain</synonym>
    <synonym>Alkohol</synonym>
    <synonym>Alkoholu etylowego</synonym>
    <synonym>Anhydrol</synonym>
    <synonym>Anhydrous alcohol</synonym>
    <synonym>Cologne spirit</synonym>
    <synonym>Cologne spirits</synonym>
    <synonym>Dehydrated alcohol</synonym>
    <synonym>Dehydrated ethanol</synonym>
    <synonym>Denatured alcohol</synonym>
    <synonym>Denatured ethanol</synonym>
    <synonym>Desinfektol EL</synonym>
    <synonym>Diluted Alcohol</synonym>
    <synonym>Distilled spirits</synonym>
    <synonym>Eth</synonym>
    <synonym>Ethanol 200 proof</synonym>
    <synonym>Ethanol solution</synonym>
    <synonym>Ethicap</synonym>
    <synonym>Ethyl alc</synonym>
    <synonym>Ethyl alcohol</synonym>
    <synonym>Ethyl alcohol anhydrous</synonym>
    <synonym>Ethyl alcohol in alcoholic beverages</synonym>
    <synonym>Ethyl alcohol usp</synonym>
    <synonym>Ethyl hydrate</synonym>
    <synonym>Ethyl hydric acid</synonym>
    <synonym>Ethyl hydroxide</synonym>
    <synonym>EtOH</synonym>
    <synonym>Fermentation alcohol</synonym>
    <synonym>Grain alcohol</synonym>
    <synonym>Hinetoless</synonym>
    <synonym>Hydroxyethane</synonym>
    <synonym>Infinity Pure</synonym>
    <synonym>Jaysol</synonym>
    <synonym>Jaysol S</synonym>
    <synonym>Lux</synonym>
    <synonym>Methylcarbinol</synonym>
    <synonym>Molasses alcohol</synonym>
    <synonym>Potato alcohol</synonym>
    <synonym>Punctilious ethyl alcohol</synonym>
    <synonym>Pyro</synonym>
    <synonym>Silent spirit</synonym>
    <synonym>Spirit</synonym>
    <synonym>Spirits of wine</synonym>
    <synonym>Spirt</synonym>
    <synonym>Synasol</synonym>
    <synonym>Tecsol</synonym>
    <synonym>Tecsol C</synonym>
    <synonym>Thanol</synonym>
    <synonym>Undenatured Ethanol</synonym>
  </synonyms>
  <chemical_formula>C2H6O</chemical_formula>
  <average_molecular_weight>46.0684</average_molecular_weight>
  <monisotopic_moleculate_weight>46.041864814</monisotopic_moleculate_weight>
  <iupac_name>ethanol</iupac_name>
  <traditional_iupac>ethyl alcohol</traditional_iupac>
  <cas_registry_number>64-17-5</cas_registry_number>
  <smiles>CCO</smiles>
  <inchi>InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3</inchi>
  <inchikey>LFQSCWFLJHTTHZ-UHFFFAOYSA-N</inchikey>
  <state>Liquid</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>-0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.79e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>-114.1 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>16.47</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-2.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>ethanol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>46.0684</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>46.041864814</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CCO</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C2H6O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>LFQSCWFLJHTTHZ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>20.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>13.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>5.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>1</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>Glycolysis / Gluconeogenesis</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00010</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Microbial metabolism in diverse environments</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec01120</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>mixed acid fermentation</name>
      <ecocyc_pathway_id>FERMENTATION-PWY</ecocyc_pathway_id>
    </pathway>
    <pathway>
      <name>ethanol degradation I</name>
      <ecocyc_pathway_id>ETOH-ACETYLCOA-ANA-PWY</ecocyc_pathway_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>136839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>144573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1050294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>142268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2810432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2810433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2810434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2895182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2895183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2895184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1145</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB00108</hmdb_id>
  <pubchem_compound_id>702</pubchem_compound_id>
  <chemspider_id>682</chemspider_id>
  <kegg_id>C00469</kegg_id>
  <chebi_id>16236</chebi_id>
  <biocyc_id>ETOH</biocyc_id>
  <het_id>OXA</het_id>
  <wikipidia>Ethanol</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>
    <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>Maddula, S., Blank, L. M., Schmid, A., Baumbach, J. I. (2009). "Detection of volatile metabolites of Escherichia coli by multi capillary column coupled ion mobility spectrometry." Anal Bioanal Chem 394:791-800.</reference_text>
      <pubmed_id>19330511</pubmed_id>
    </reference>
    <reference>
      <reference_text>Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva.  J Dent Res. 2002 Jun;81(6):422-7.</reference_text>
      <pubmed_id>12097436</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gordon Z, Parsons CL, Monga M: Intravesical ethanol test: an ineffective measure of bladder hyperpermeability. Urology. 2003 Mar;61(3):555-7.</reference_text>
      <pubmed_id>12639646</pubmed_id>
    </reference>
    <reference>
      <reference_text>Huang JS, She QB, Crilly KS, Kiss Z: Ethanol, Zn2+ and insulin interact as progression factors to enhance DNA synthesis synergistically in the presence of Ca2+ and other cell cycle initiators in fibroblasts. Biochem J. 2000 Feb 15;346 Pt 1:241-7.</reference_text>
      <pubmed_id>10657263</pubmed_id>
    </reference>
    <reference>
      <reference_text>Friedman GD, Klatsky AL, Siegelaub AB: Alcohol, tobacco, and hypertension.  Hypertension. 1982 Sep-Oct;4(5 Pt 2):III143-50.</reference_text>
      <pubmed_id>7049929</pubmed_id>
    </reference>
    <reference>
      <reference_text>Uemura M, Lehmann WD, Schneider W, Seitz HK, Benner A, Keppler-Hafkemeyer A, Hafkemeyer P, Kojima H, Fujimoto M, Tsujii T, Fukui H, Keppler D: Enhanced urinary excretion of cysteinyl leukotrienes in patients with acute alcohol intoxication. Gastroenterology. 2000 Jun;118(6):1140-8.</reference_text>
      <pubmed_id>10833489</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hemmingsen R, Barry DI, Hertz MM, Klinken L: Cerebral blood flow and oxygen consumption during ethanol withdrawal in the rat. Brain Res. 1979 Sep 14;173(2):259-69.</reference_text>
      <pubmed_id>573652</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lopez JM, Bombi JA, Valderrama R, Gimenez A, Pares A, Caballeria J, Imperial S, Navarro S: Effects of prolonged ethanol intake and malnutrition on rat pancreas.  Gut. 1996 Feb;38(2):285-92.</reference_text>
      <pubmed_id>8801213</pubmed_id>
    </reference>
    <reference>
      <reference_text>Yamashina S, Ikejima K, Enomoto N, Takei Y, Sato N: [Ethanol changes sensitivity of Kupffer cells to endotoxin]  Nihon Arukoru Yakubutsu Igakkai Zasshi. 2003 Oct;38(5):415-24.</reference_text>
      <pubmed_id>14639920</pubmed_id>
    </reference>
    <reference>
      <reference_text>Aye MM, Ma C, Lin H, Bower KA, Wiggins RC, Luo J: Ethanol-induced in vitro invasion of breast cancer cells: the contribution of MMP-2 by fibroblasts. Int J Cancer. 2004 Dec 10;112(5):738-46.</reference_text>
      <pubmed_id>15386367</pubmed_id>
    </reference>
    <reference>
      <reference_text>De Martinis BS, de Paula CM, Braga A, Moreira HT, Martin CC: Alcohol distribution in different postmortem body fluids.  Hum Exp Toxicol. 2006 Feb;25(2):93-7.</reference_text>
      <pubmed_id>16539214</pubmed_id>
    </reference>
    <reference>
      <reference_text>Pohorecky LA: Influence of alcohol on peripheral neurotransmitter function.  Fed Proc. 1982 Jun;41(8):2452-5.</reference_text>
      <pubmed_id>6123447</pubmed_id>
    </reference>
    <reference>
      <reference_text>Dean RA, Zhang J, Brzezinski MR, Bosron WF: Tissue distribution of cocaine methyl esterase and ethyl transferase activities: correlation with carboxylesterase protein. J Pharmacol Exp Ther. 1995 Nov;275(2):965-71.</reference_text>
      <pubmed_id>7473189</pubmed_id>
    </reference>
    <reference>
      <reference_text>Elias AN, Meshkinpour H, Valenta LJ, Grossman MK: Pseudo-Cushing's syndrome: the role of alcohol.  J Clin Gastroenterol. 1982 Apr;4(2):137-9.</reference_text>
      <pubmed_id>6282953</pubmed_id>
    </reference>
    <reference>
      <reference_text>Henriksson J, Knol M: A single bout of exercise is followed by a prolonged decrease in the interstitial glucose concentration in skeletal muscle. Acta Physiol Scand. 2005 Dec;185(4):313-20.</reference_text>
      <pubmed_id>16266372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Rosdahl H, Lind L, Millgard J, Lithell H, Ungerstedt U, Henriksson J: Effect of physiological hyperinsulinemia on blood flow and interstitial glucose concentration in human skeletal muscle and adipose tissue studied by microdialysis. Diabetes. 1998 Aug;47(8):1296-301.</reference_text>
      <pubmed_id>9703331</pubmed_id>
    </reference>
    <reference>
      <reference_text>Boschmann M, Adams F, Schaller K, Franke G, Sharma AM, Klaus S, Luft FC, Jordan J: Hemodynamic and metabolic responses to interstitial angiotensin II in normal weight and obese men. J Hypertens. 2006 Jun;24(6):1165-71.</reference_text>
      <pubmed_id>16685217</pubmed_id>
    </reference>
    <reference>
      <reference_text>Igawa Y, Satoh T, Mizusawa H, Seki S, Kato H, Ishizuka O, Nishizawa O: The role of capsaicin-sensitive afferents in autonomic dysreflexia in patients with spinal cord injury. BJU Int. 2003 May;91(7):637-41.</reference_text>
      <pubmed_id>12699475</pubmed_id>
    </reference>
    <reference>
      <reference_text>Enocksson S, Shimizu M, Lonnqvist F, Nordenstrom J, Arner P: Demonstration of an in vivo functional beta 3-adrenoceptor in man.  J Clin Invest. 1995 May;95(5):2239-45.</reference_text>
      <pubmed_id>7738189</pubmed_id>
    </reference>
    <reference>
      <reference_text>Collins JW, Macdermott S, Bradbrook RA, Keeley FX Jr, Timoney AG: Is using ethanol-glycine irrigating fluid monitoring and 'good surgical practice' enough to prevent harmful absorption during transurethral resection of the prostate? BJU Int. 2006 Jun;97(6):1247-51.</reference_text>
      <pubmed_id>16686720</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sokolik VV, Chursina VS, Artemchuk AA, Artemchuk AF, Bozhko GKh: [Depression of serum esterase and lipoprotein lipase activities in acute and longitudinal actions of ethanol] Biomed Khim. 2006 Jan-Feb;52(1):95-100.</reference_text>
      <pubmed_id>16739925</pubmed_id>
    </reference>
    <reference>
      <reference_text>Snyder R, Kalf GF: A perspective on benzene leukemogenesis. Crit Rev Toxicol. 1994;24(3):177-209.</reference_text>
      <pubmed_id>7945890</pubmed_id>
    </reference>
    <reference>
      <reference_text>McDonnell G, Russell AD: Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev. 1999 Jan;12(1):147-79.</reference_text>
      <pubmed_id>9880479</pubmed_id>
    </reference>
    <reference>
      <reference_text>Barceloux DG, Bond GR, Krenzelok EP, Cooper H, Vale JA: American Academy of Clinical Toxicology practice guidelines on the treatment of methanol poisoning. J Toxicol Clin Toxicol. 2002;40(4):415-46.</reference_text>
      <pubmed_id>12216995</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hingson R, Winter M: Epidemiology and consequences of drinking and driving. Alcohol Res Health. 2003;27(1):63-78.</reference_text>
      <pubmed_id>15301401</pubmed_id>
    </reference>
    <reference>
      <reference_text>Chastain G: Alcohol, neurotransmitter systems, and behavior. J Gen Psychol. 2006 Oct;133(4):329-35.</reference_text>
      <pubmed_id>17128954</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference>Lashley, David.  Process for producing an alcoholic sugar cane juice beverage.    U.S.  (1988),     3 pp.  CODEN: USXXAM  US  4784859  A  19881115  CAN 110:113222  AN 1989:113222  </synthesis_reference>
  <msds_url>http://hmdb.ca/system/metabolites/msds/000/000/074/original/HMDB00108.pdf?1358463473</msds_url>
  <enzymes>
    <enzyme>
      <name>Aldehyde-alcohol dehydrogenase</name>
      <uniprot_id>P0A9Q7</uniprot_id>
      <uniprot_name>ADHE_ECOLI</uniprot_name>
      <gene_name>adhE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0A9Q7.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>S-(hydroxymethyl)glutathione dehydrogenase</name>
      <uniprot_id>P25437</uniprot_id>
      <uniprot_name>FRMA_ECOLI</uniprot_name>
      <gene_name>frmA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P25437.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Alcohol dehydrogenase, propanol-preferring</name>
      <uniprot_id>P39451</uniprot_id>
      <uniprot_name>ADHP_ECOLI</uniprot_name>
      <gene_name>adhP</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P39451.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>predicted Fe-containing alcohol dehydrogenase, Pfam00465 family</name>
      <uniprot_id>P37686</uniprot_id>
      <uniprot_name/>
      <gene_name>yiaY</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P37686.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>ethanol dehydrogenase involved in ethanolamine utilization; aldehyde reductase, converts acetaldehyde to ethanol</name>
      <uniprot_id>P76553</uniprot_id>
      <uniprot_name/>
      <gene_name>eutG</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P76553.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
    <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>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>Ethanol + NAD &lt;&gt; Acetaldehyde + Hydrogen ion + NADH</reaction_text>
    <kegg_reaction_id>R00754</kegg_reaction_id>
    <ecocyc_id>ALCOHOL-DEHYDROG-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Ethanol + NAD &lt;&gt; Acetaldehyde + NADH + Hydrogen ion</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>ALCOHOL-DEHYDROG-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Ethanol + NAD &lt;&gt; Acetaldehyde + Hydrogen ion + NADH</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Ethanol + NAD &lt;&gt; Acetaldehyde + Hydrogen ion + NADH</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
