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Identification
YMDB IDYMDB00056
NameAcetic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAcetic acid, also known as glacial acetate or vinegar, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Acetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Acetic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • Acetate
  • ACETATE ION
  • acetic acid
  • Acetic acid glacial
  • Acetic acid, glacial
  • Acid glacial, acetic
  • Acid, acetic
  • Acid, glacial acetic
  • Acide acetique
  • AcOH
  • Azetat
  • CH3-COOH
  • CH3CO2H
  • e 260
  • e-260
  • e260
  • Essigsaeure
  • Ethanoat
  • Ethanoate
  • Ethanoic acid
  • Ethoate
  • Ethoic acid
  • Ethylate
  • Ethylic acid
  • Glacial acetate
  • Glacial acetic acid
  • Glacial, acetic acid
  • HOAc
  • Hydrocortisone acetate
  • INS no. 260
  • Kyselina octova
  • MeCO2h
  • MeCOOH
  • Methanecarboxylate
  • Methanecarboxylic acid
  • Vinegar
  • Vinegar acid
  • Acetasol
CAS number64-19-7
WeightAverage: 60.052
Monoisotopic: 60.021129372
InChI KeyQTBSBXVTEAMEQO-UHFFFAOYSA-N
InChIInChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
IUPAC Nameacetic acid
Traditional IUPAC Nameacetic acid
Chemical FormulaC2H4O2
SMILES[H]OC(=O)C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point16.6 °C
Experimental Properties
PropertyValueReference
Water Solubility1000 mg/mL at 25 oC [MERCK INDEX (1996)]PhysProp
LogP-0.17 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility323 g/LALOGPS
logP-0.12ALOGPS
logP-0.22ChemAxon
logS0.73ALOGPS
pKa (Strongest Acidic)4.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity12.64 m³·mol⁻¹ChemAxon
Polarizability5.34 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Endoplasmic Reticulum, Extracellular, Mitochondrion, Nucleus
Organoleptic Properties
Flavour/OdourSource
PungentFDB008299
SharpFDB008299
SourFDB008299
VinegarFDB008299
SMPDB Pathways
Cysteine MetabolismPW002383 ThumbThumb?image type=greyscaleThumb?image type=simple
Ether lipid metabolismPW002492 ThumbThumb?image type=greyscaleThumb?image type=simple
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
Methionine metabolism and salvagePW002384 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Ether lipid metabolismec00565 Map00565
Fatty acid biosynthesisec00061 Map00061
Glycolysis / Gluconeogenesisec00010 Map00010
Methane metabolismec00680 Map00680
Pyruvate metabolismec00620 Map00620
SMPDB Reactions
Selenocysteine + AcetylhomoserineSelenocystathionine + Acetic acid
Hydrogen sulfide + O-acetyl-L-serineL-Cysteine + Acetic acid + hydron
Cytidine monophosphate + 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholineAcetic acid + hydron + Lyso-PAF C-16
KEGG Reactions
water + 4-Acetamidobutanoic acidAcetic acid + gamma-Aminobutyric acid
Acetic acid + hydron + Coenzyme AAcetyl-CoA + water
Acetyl-CoA + waterAcetic acid + hydron + Coenzyme A
Adenosine triphosphate + Acetic acid + Coenzyme AAdenosine monophosphate + Pyrophosphate + Acetyl-CoA
Adenosine triphosphate + Acetic acid + Coenzyme AAdenosine monophosphate + Pyrophosphate + Acetyl-CoA
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
25775 ± 1289 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
18500 ± 16500 µM Synthetic medium with 1% glucose and 0.1% yeast extractaerobicBaker's yeastPMID: 16623706
Conversion Details Here
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
5000 ± 5000 µM Synthetic medium with 1% glucose and 0.1% yeast extractaerobicBaker's yeastPMID: 16623706
Conversion Details Here
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • Abadjieva, A., Pauwels, K., Hilven, P., Crabeel, M. (2001). "A new yeast metabolon involving at least the two first enzymes of arginine biosynthesis: acetylglutamate synthase activity requires complex formation with acetylglutamate kinase." J Biol Chem 276:42869-42880.11553611
  • 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:Law, David John. Process for the preparation of carboxylic acids and/or derivatives thereof. PCT Int. Appl. (2007), 14pp.
External Links:
ResourceLink
CHEBI ID15366
HMDB IDHMDB00042
Pubchem Compound ID176
Kegg IDC00033
ChemSpider ID171
FOODB IDFDB008299
WikipediaAcetic_acid
BioCyc IDACET

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(P)(+) + H(2)O = an acid + NAD(P)H
Gene Name:
ALD2
Uniprot ID:
P47771
Molecular weight:
55187.39844
Reactions
An aldehyde + NAD(P)(+) + H(2)O → an acid + NAD(P)H.
General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(+) + H(2)O = an acid + NADH
Gene Name:
ALD4
Uniprot ID:
P46367
Molecular weight:
56723.19922
Reactions
An aldehyde + NAD(+) + H(2)O → an acid + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(P)(+) + H(2)O = an acid + NAD(P)H
Gene Name:
ALD3
Uniprot ID:
P54114
Molecular weight:
55384.80078
Reactions
An aldehyde + NAD(P)(+) + H(2)O → an acid + NAD(P)H.
General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(+) + H(2)O = an acid + NADH
Gene Name:
ALD6
Uniprot ID:
P54115
Molecular weight:
54413.69922
Reactions
An aldehyde + NAD(+) + H(2)O → an acid + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
Minor mitochondrial aldehyde dehydrogenase isoform. Plays a role in regulation or biosynthesis of electron transport chain components. Involved in the biosynthesis of acetate during anaerobic growth on glucose
Gene Name:
ALD5
Uniprot ID:
P40047
Molecular weight:
56620.39844
Reactions
An aldehyde + NAD(+) + H(2)O → an acid + NADH.
An aldehyde + NADP(+) + H(2)O → an acid + NADPH.
General function:
Involved in catalytic activity
Specific function:
Presumably involved in regulating the intracellular acetyl-CoA pool for fatty acid and cholesterol synthesis and fatty acid oxidation. It may be involved in overall regulation of acetylation during melatonin synthesis
Gene Name:
ACH1
Uniprot ID:
P32316
Molecular weight:
58711.5
Reactions
Acetyl-CoA + H(2)O → CoA + acetate.
General function:
Involved in acetate-CoA ligase activity
Specific function:
Catalyzes the production of acetyl-CoA. Provides the acetyl-CoA source for histone acetylation in the nucleus. "Aerobic" isozyme of acetyl-coenzyme A synthetase, which supports growth on nonfermentable carbon sources such as glycerol and ethanol. May be required for assimilation of ethanol and acetate
Gene Name:
ACS1
Uniprot ID:
Q01574
Molecular weight:
79140.10156
Reactions
ATP + acetate + CoA → AMP + diphosphate + acetyl-CoA.
General function:
Involved in acetate-CoA ligase activity
Specific function:
Catalyzes the production of acetyl-CoA. Provides the acetyl-CoA source for histone acetylation in the nucleus. "Anaerobic" isozyme of acetyl-coenzyme A synthetase, which is required for growth on fermentable carbon sources such as glucose. May be involved in the PDH (pyruvate dehydrogenase complex) bypass
Gene Name:
ACS2
Uniprot ID:
P52910
Molecular weight:
75491.10156
Reactions
ATP + acetate + CoA → AMP + diphosphate + acetyl-CoA.
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate
Gene Name:
Not Available
Uniprot ID:
P53206
Molecular weight:
42800.5
Reactions
O(3)-acetyl-L-serine + H(2)S → L-cysteine + acetate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
Not Available
Uniprot ID:
Q04533
Molecular weight:
74312.70313
Reactions
O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
Transforms O-acetylhomoserine into homocysteine and O- acetylserine into cysteine
Gene Name:
MET17
Uniprot ID:
P06106
Molecular weight:
48671.39844
Reactions
O-acetyl-L-homoserine + methanethiol → L-methionine + acetate.
O(3)-acetyl-L-serine + H(2)S → L-cysteine + acetate.
General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
STR2
Uniprot ID:
P47164
Molecular weight:
72349.89844
Reactions
O(4)-succinyl-L-homoserine + L-cysteine → L-cystathionine + succinate.
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the N-acetamido groups of N-acetyl-D- glucosamine residues in chitin
Gene Name:
CDA1
Uniprot ID:
Q06702
Molecular weight:
34642.0
Reactions
Chitin + H(2)O → chitosan + acetate.
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the N-acetamido groups of N-acetyl-D- glucosamine residues in chitin
Gene Name:
CDA2
Uniprot ID:
Q06703
Molecular weight:
35692.80078
Reactions
Chitin + H(2)O → chitosan + acetate.
General function:
Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:
Involved in the second step of GPI biosynthesis. De-N- acetylation of N-acetylglucosaminyl-phosphatidylinositol
Gene Name:
GPI12
Uniprot ID:
P23797
Molecular weight:
35445.60156
Reactions
6-(N-acetyl-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H(2)O → 6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate.
General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde
Gene Name:
Not Available
Uniprot ID:
P40363
Molecular weight:
33934.0
Reactions
S-formylglutathione + H(2)O → glutathione + formate.
4-methylumbelliferyl acetate + H2O → 4-methylumbelliferone + acetate
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

Transporters

General function:
Involved in protein binding
Specific function:
May be involved in protein sorting and cell wall formation
Gene Name:
BPH1
Uniprot ID:
P25356
Molecular weight:
250870.0
General function:
Involved in acetate transmembrane transporter activity
Specific function:
Transporter protein required for ammonia export and acetate uptake and resistance. Necessary for up-regulation and down-regulation of meiotic plaque (MP) component levels in a dependency on external acetate. Has a role in ascus formation
Gene Name:
ADY2
Uniprot ID:
P25613
Molecular weight:
30725.90039