You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00883
NameEthanol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEthanol (EtOH), also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a versatile solvent, miscible with water and with many organic solvents, including acetic acid, acetone, benzene, carbon tetrachloride, chloroform, diethyl ether, ethylene glycol, glycerol, nitromethane, pyridine, and toluene. In chemistry, ethanol is both an essential solvent and a feedstock for the synthesis of other products. It has a long history as a fuel for heat and light, and more recently as a fuel for internal combustion engines. Ethanol can be prepared either by industrial fermentation from yeast or by conversion by from ethylene. Ethanol is the primary alcohol found in alcoholic beverages. It is also used in scents, flavorings, colorings, and medicines.
Alcoholic beverages such as wine, beer, or distilled spirits all use yeast at some stage of their production. Alcoholic beverages vary considerably in ethanol content and in foodstuffs they are produced from. Most alcoholic beverages can be broadly classified as fermented beverages, beverages made by the action of yeast on sugary foodstuffs, or distilled beverages, beverages whose preparation involves concentrating the ethanol in fermented beverages by distillation. The ethanol content of a beverage is usually measured in terms of the volume fraction of ethanol in the beverage, expressed either as a percentage (~5% for beers, ~12% for wines) or in alcoholic proof units (40-80 proof for many spirits). Fermented beverages can be broadly classified by the grains, fruits or vegetables they are fermented from. Beers are made from cereal grains or other starchy materials, wines and ciders from fruit juices, and meads from honey. Distilled beverages are made by distilling fermented beverages. Broad categories of distilled beverages include whiskeys, distilled from fermented cereal grains; brandies, distilled from fermented fruit juices; and rum, distilled from fermented molasses or sugarcane juice. Vodka and similar neutral grain spirits can be distilled from any fermented material (grain or potatoes are most common); these spirits are so thoroughly distilled that no tastes from the particular starting material remain. Numerous other spirits and liqueurs are prepared by infusing flavors from fruits, herbs, and spices into distilled spirits. A traditional example is gin, which is created by infusing juniper berries into a neutral grain alcohol. Alcoholic beverages can also be made into culinary/household vinegar: Wine and cider vinegar are both named for their respective source alcohols, whereas malt vinegar is derived from beer.
Ethanol is also a psychoactive drug and one of the oldest known recreational drugs. Ethanol binds to acetylcholine, GABA, serotonin, and NMDA receptors with depressant effects on the central nervous system.
Structure
Thumb
Synonyms
  • 1-Hydroxyethane
  • Aethanol
  • Aethylalkohol
  • Alcohol
  • Ethyl alc
  • Ethyl alcohol
  • Ethyl hydrate
  • Ethyl hydroxide
  • Hydroxyethane
  • [CH2Me(OH)]
  • [OEtH]
  • Alcohol etilico
  • Alcool ethylique
  • Alkohol
  • C2H5OH
  • Dehydrated ethanol
  • Etanol
  • EtOH
  • Methylcarbinol
  • Spiritus vini
  • Anhydrous ethanol
  • Absolute alcohol
  • Absolute ethanol
  • Absolute ethyl alcohol
  • Alcare hand degermer
  • Alcohols
  • Alcool etilico
  • Algrain
  • Alkoholu etylowego
  • Anhydrol
  • Anhydrous alcohol
  • Cologne spirit
  • Cologne spirits
  • Dehydrated alcohol
  • Denatured alcohol
  • Denatured ethanol
  • Desinfektol el
  • Diluted alcohol
  • Distilled spirits
  • Ethanol 200 proof
  • Ethanol solution
  • Ethicap
  • Ethyl alcohol anhydrous
  • Ethyl alcohol in alcoholic beverages
  • Ethyl alcohol usp
  • Fermentation alcohol
  • Grain alcohol
  • Hinetoless
  • Infinity pure
  • Jaysol
  • Jaysol S
  • Lux
  • Molasses alcohol
  • Potato alcohol
  • Punctilious ethyl alcohol
  • Pyro
  • Silent spirit
  • Spirit
  • Spirits OF wine
  • Spirt
  • Synasol
  • Tecsol
  • Tecsol C
  • Thanol
  • Undenatured ethanol
  • Alcohol, absolute
  • Alcohol, ethyl
  • Alcohol, grain
CAS number64-17-5
WeightAverage: 46.0684
Monoisotopic: 46.041864814
InChI KeyLFQSCWFLJHTTHZ-UHFFFAOYSA-N
InChIInChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3
IUPAC Nameethanol
Traditional IUPAC Nameethyl alcohol
Chemical FormulaC2H6O
SMILES[H]OC([H])([H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-114.1 °C
Experimental Properties
PropertyValueReference
Water Solubility1000 mg/mL at 25 oC [RIDDICK,JA et al. (1986)]PhysProp
LogP-0.31 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility579 g/LALOGPS
logP-0.4ALOGPS
logP-0.16ChemAxon
logS1.1ALOGPS
pKa (Strongest Acidic)16.47ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity13.01 m³·mol⁻¹ChemAxon
Polarizability5.3 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
AlcoholicFDB009376
EtherealFDB009376
MedicalFDB009376
StrongFDB009376
SweetFDB009376
SMPDB Pathways
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycolysis / Gluconeogenesisec00010 Map00010
Pyruvate metabolismec00620 Map00620
SMPDB Reactions
Acetaldehyde + hydron + NADHEthanol + NAD
Glycerophosphocholine + waterEthanol + Choline
KEGG Reactions
Ethanol + Acetyl-CoAEthyl acetate + Coenzyme A
Ethanol + NADNADH + Acetaldehyde + hydron
NADH + Acetaldehyde + hydronEthanol + NAD
water + Ethyl acetateEthanol + Acetic acid + hydron
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
325823 ± 68594 µM YEPD media 200g/L glucoseanaerobic;30C;12hBrewer's yeastPMID: 3513699
583052 ± 120040 µM YEPD media 200g/L glucoseanaerobic;30C;24hBrewer's yeastPMID: 3513699
1406185 ± 291526 µM YEPD media 200g/L glucoseanaerobic;30C;48hBrewer's yeastPMID: 3513699
1825 ± 91 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
868282 ± 8000 µM hops, malted barleyanaerobicBrewer's yeastPMID: 16448171
291526 ± 17149 µM YEPD media 200g/L glucoseanaerobic;30C;12hBrewer's yeastPMID: 3513699
943173 ± 17149 µM YEPD media 200g/L glucoseanaerobic;30C;24hBrewer's yeastPMID: 3513699
1920643 ± 171486 µM YEPD media 200g/L glucoseanaerobic;30C;48hBrewer's yeastPMID: 3513699
846575 ± 6946 µM hops, malted barleyanaerobicBrewer's yeastAlcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
2300946 ± 4341 µM grape juiceanaerobicBrewer's yeastAlcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
1500 ± 1000 µM Synthetic medium with 1% glucose and 0.1% yeast extractaerobicBrewer's yeastPMID: 16623706
543 ± 0 uM Glucose 1.0 g/l as carbon sourceAerobic, 25 oCBrewer's yeastPMID: 5516454
2952 ± 0 uM Glucose 2.0 g/l as carbon sourceAerobic, 25 oCBrewer's yeastPMID: 5516454
12807 ± 0 uM Glucose 5.0 g/l as carbon sourceAerobic, 25 oCBrewer's yeastPMID: 5516454
31258 ± 0 uM Glucose 10.0 g/l as carbon sourceAerobic, 25 oCBrewer's yeastPMID: 5516454
39072 ± 0 uM Glucose 50.0 g/l as carbon sourceAerobic, 25 oCBrewer's yeastPMID: 5516454
195 ± 0 uM Galatose 1.0 g/l as carbon sourceAerobic, 25 oCBrewer's yeastPMID: 5516454
304 ± 0 uM Galactose 2.0 g/l as carbon sourceAerobic, 25 oCBrewer's yeastPMID: 5516454
3668 ± 0 uM Galactose 5.0 g/l as carbon sourceAerobic, 25 oCBrewer's yeastPMID: 5516454
12677 ± 0 uM Galactose 10.0 g/l as carbon sourceAerobic, 25 oCBrewer's yeastPMID: 5516454
23574 ± 0 uM Galactose 50.0 g/l as carbon sourceAerobic, 25 oCBrewer's yeastPMID: 5516454
Conversion Details Here
Spectra
Spectra
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Schwartz, J. M., Kanehisa, M. (2006). "Quantitative elementary mode analysis of metabolic pathways: the example of yeast glycolysis." BMC Bioinformatics 7:186.16584566
  • Goncalves, P., Planta, R. J. (1998). "Starting up yeast glycolysis." Trends Microbiol 6:314-319.9746941
  • Almeida, C., Duarte, I. F., Barros, A., Rodrigues, J., Spraul, M., Gil, A. M. (2006). "Composition of beer by 1H NMR spectroscopy: effects of brewing site and date of production." J Agric Food Chem 54:700-706.16448171
  • Dombek, K. M., Ingram, L. O. (1986). "Determination of the intracellular concentration of ethanol in Saccharomyces cerevisiae during fermentation." Appl Environ Microbiol 51:197-200.3513699
  • Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
  • Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
  • Leskovac, V., Trivic, S., Pericin, D. (2002). "The three zinc-containing alcohol dehydrogenases from baker's yeast, Saccharomyces cerevisiae." FEMS Yeast Res 2:481-494.12702265
  • Fukuda, K., Kiyokawa, Y., Yanagiuchi, T., Wakai, Y., Kitamoto, K., Inoue, Y., Kimura, A. (2000). "Purification and characterization of isoamyl acetate-hydrolyzing esterase encoded by the IAH1 gene of Saccharomyces cerevisiae from a recombinant Escherichia coli." Appl Microbiol Biotechnol 53:596-600.10855721
  • Verstrepen, K. J., Van Laere, S. D., Vanderhaegen, B. M., Derdelinckx, G., Dufour, J. P., Pretorius, I. S., Winderickx, J., Thevelein, J. M., Delvaux, F. R. (2003). "Expression levels of the yeast alcohol acetyltransferase genes ATF1, Lg-ATF1, and ATF2 control the formation of a broad range of volatile esters." Appl Environ Microbiol 69:5228-5237.12957907
  • Dickinson, J. R., Salgado, L. E., Hewlins, M. J. (2003). "The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae." J Biol Chem 278:8028-8034.12499363
  • Xu, Z., Tsurugi, K. (2006). "A potential mechanism of energy-metabolism oscillation in an aerobic chemostat culture of the yeast Saccharomyces cerevisiae." FEBS J 273:1696-1709.16623706
Synthesis Reference:Hennell, H. (1828). On the mutual action of sulfuric acid and alcohol, and on the nature of the process by which ether is formed. Philosophical Transactions 118: 365.
External Links:
ResourceLink
CHEBI ID16236
HMDB IDHMDB00108
Pubchem Compound ID702
Kegg IDC00469
ChemSpider ID682
FOODB IDFDB009376
WikipediaEthanol
BioCyc IDETOH

Enzymes

General function:
Involved in zinc ion binding
Specific function:
An alcohol + NAD(+) = an aldehyde or ketone + NADH
Gene Name:
ADH3
Uniprot ID:
P07246
Molecular weight:
40369.19922
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in zinc ion binding
Specific function:
Oxidizes long-chain alcohols and, in the presence of glutathione, is able to oxidize formaldehyde. Is responsible for yeast resistance to formaldehyde
Gene Name:
SFA1
Uniprot ID:
P32771
Molecular weight:
41041.69922
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) → S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in zinc ion binding
Specific function:
This isozyme preferentially catalyzes the conversion of primary unbranched alcohols to their corresponding aldehydes. Also also shows activity toward secondary alcohols
Gene Name:
ADH1
Uniprot ID:
P00330
Molecular weight:
36849.0
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
Reduces acetaldehyde to ethanol during glucose fermentation. Specific for ethanol. Shows drastically reduced activity towards primary alcohols from 4 carbon atoms upward. Isomers of aliphatic alcohol, as well as secondary alcohols and glycerol are not used at all
Gene Name:
ADH4
Uniprot ID:
P10127
Molecular weight:
41141.69922
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in zinc ion binding
Specific function:
An alcohol + NAD(+) = an aldehyde or ketone + NADH
Gene Name:
ADH5
Uniprot ID:
P38113
Molecular weight:
37647.89844
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in zinc ion binding
Specific function:
This isozyme preferentially catalyzes the conversion of ethanol to acetaldehyde. Acts on a variety of primary unbranched aliphatic alcohols
Gene Name:
ADH2
Uniprot ID:
P00331
Molecular weight:
36731.60156
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in alcohol O-acetyltransferase activity
Specific function:
Catalyzes the esterification of isoamyl alcohol and various other alcohols by acetyl-CoA
Gene Name:
ATF1
Uniprot ID:
P40353
Molecular weight:
61035.5
Reactions
Acetyl-CoA + an alcohol → CoA + an acetyl ester.
General function:
Involved in alcohol O-acetyltransferase activity
Specific function:
Acetyl-CoA + an alcohol = CoA + an acetyl ester
Gene Name:
ATF2
Uniprot ID:
P53296
Molecular weight:
61897.5
Reactions
Acetyl-CoA + an alcohol → CoA + an acetyl ester.
General function:
Involved in protein binding
Specific function:
Glycerophosphocholine glycerophosphodiesterase responsible for the hydrolysis of intracellular glycerophosphocholine into glycerol-phosphate and choline. The choline is used for phosphatidyl-choline synthesis. Required for utilization of glycerophosphocholine as phosphate source
Gene Name:
GDE1
Uniprot ID:
Q02979
Molecular weight:
138013.0
Reactions
A glycerophosphodiester + H(2)O → an alcohol + sn-glycerol 3-phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the irreversible reduction of the cytotoxic compound methylglyoxal (MG) to (R)-lactaldehyde as an alternative to detoxification of MG by glyoxalase I GLO1. MG is synthesized via a bypath of glycolysis from dihydroxyacetone phosphate and is believed to play a role in cell cycle regulation and stress adaptation
Gene Name:
GRE2
Uniprot ID:
Q12068
Molecular weight:
38169.19922
Reactions
Lactaldehyde + NADP(+) → methylglyoxal + NADPH.
3-methylbutanol + NAD(P)+ → 3-methylbutanal + NAD(P)H + H+
General function:
Involved in zinc ion binding
Specific function:
NADP-dependent alcohol dehydrogenase with a broad substrate specificity
Gene Name:
ADH7
Uniprot ID:
P25377
Molecular weight:
39348.19922
Reactions
An alcohol + NADP(+) → an aldehyde + NADPH.
General function:
Involved in zinc ion binding
Specific function:
NADP-dependent alcohol dehydrogenase with a broad substrate specificity
Gene Name:
ADH6
Uniprot ID:
Q04894
Molecular weight:
39617.30078
Reactions
An alcohol + NADP(+) → an aldehyde + NADPH.
General function:
Involved in hydrolase activity
Specific function:
Plays a crucial role in the hydrolysis of isoamyl acetate in sake mash
Gene Name:
IAH1
Uniprot ID:
P41734
Molecular weight:
27346.0
Reactions