Record Information
Version2.0
Creation Date2012-05-31 09:55:48 -0600
Update Date2015-09-13 12:56:05 -0600
Secondary Accession Numbers
  • ECMDB00042
Identification
Name:Acetic acid
Description:Acetic acid is one of the simplest carboxylic acids. The acetyl group, derived from acetic acid, is fundamental to the biochemistry of virtually all forms of life. When bound to coenzyme A it forms acetyl-CoA, which is central to the metabolism of carbohydrates and fats. However, the concentration of free acetic acid in cells is kept at a low level to avoid disrupting the control of the pH of the cell contents. Acetic acid is produced and excreted by certain bacteria, notably the Acetobacter genus and Clostridium acetobutylicum. These bacteria are found universally in foodstuffs, water, and soil, and acetic acid is produced naturally as fruits and some other foods spoil. (Wikipedia) Acetic acid, or more accurately, acetate, a derivative of acetic acid, can be produced by E. coli through fermentation in glucose metabolism. (KEGG, PMID 18600996)
Structure
Thumb
Synonyms:
  • Acetate
  • Acetic acid
  • Ethanoate
  • Ethanoic acid
  • Ethylate
  • Ethylic acid
  • Glacial acetate
  • Glacial acetic acid
  • Kyselina octova
  • Methanecarboxylate
  • Methanecarboxylic acid
  • Vinegar
  • Vinegar acid
Chemical Formula:C2H4O2
Weight:Average: 60.052
Monoisotopic: 60.021129372
InChI Key:QTBSBXVTEAMEQO-UHFFFAOYSA-N
InChI:InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
CAS number:64-19-7
IUPAC Name:acetic acid
Traditional IUPAC Name:acetic acid
SMILES:CC(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as carboxylic acids. These 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
State:Liquid
Charge:-1
Melting point:16.6 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000.0 mg/mL [MERCK INDEX (1996)]PhysProp
LogP:-0.17 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility323.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity12.64 m3·mol-1ChemAxon
Polarizability5.34 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Citric acid <> Acetic acid + Oxalacetic acid
Acetoacetic acid + Acetyl-CoA > Acetoacetyl-CoA + Acetic acid
Acetyl-CoA + Butyric acid > Acetic acid + Butyryl-CoA
Acetyl-CoA + Hexanoate (N-C6:0) > Acetic acid + Hexanoyl-CoA
O-Acetylserine + Hydrogen sulfide <> Acetic acid + L-Cysteine + Hydrogen ion
Acetic acid + Adenosine triphosphate <> Acetylphosphate + ADP
Water + UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine <> Acetic acid + UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine
N-Acetyl-D-Glucosamine 6-Phosphate + Water <> Acetic acid + Glucosamine 6-phosphate
Water + Pyruvic acid + Ubiquinone-8 > Acetic acid + Carbon dioxide + Ubiquinol-8
Acetaldehyde + Water + NAD > Acetic acid +2 Hydrogen ion + NADH
Acetaldehyde + Water + NADP > Acetic acid +2 Hydrogen ion + NADPH
N-Acetylornithine + Water <> Acetic acid + Ornithine + L-Ornithine
N-Acetyl-L-glutamate 5-semialdehyde + Water > Acetic acid + L-Glutamic-gamma-semialdehyde
Acetic acid + Adenosine triphosphate + Coenzyme A <> Acetyl-CoA + Adenosine monophosphate + Pyrophosphate
Adenosine triphosphate + Acetic acid + Coenzyme A <> Adenosine monophosphate + Pyrophosphate + Acetyl-CoA
Adenosine triphosphate + Acetic acid <> ADP + Acetylphosphate
Adenosine triphosphate + Acetic acid <> Pyrophosphate + Acetyl adenylate
Acetylphosphate + Water <> Acetic acid + Phosphate
Phosphonoacetate + Water <> Acetic acid + Phosphate
Citric acid <> Acetic acid + Oxalacetic acid
N-Acetylornithine + Water <> Acetic acid + Ornithine
O-Acetylserine + Hydrogen sulfide <> L-Cysteine + Acetic acid
Butanoyl-CoA + Acetic acid <> Butyric acid + Acetyl-CoA
Acetoacetyl-CoA + Acetic acid <> Acetoacetic acid + Acetyl-CoA
N-Acetyl-D-Glucosamine 6-Phosphate + Water <> Glucosamine 6-phosphate + Acetic acid
O-Acetylserine + Thiosulfate <> Cysteine-S-sulfate + Acetic acid
Pyruvic acid + Ubiquinone-1 + Water <> Acetic acid + Ubiquinol-8 + Carbon dioxide
o-acetyl-l-homoserine + L-Cysteine <> L-Cystathionine + Acetic acid
O-Acetylserine + Hydrogen selenide <> Selenocysteine + Acetic acid
UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine + Water <> UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine + Acetic acid
O-Acetylserine + Thiosulfate + Thioredoxin + Hydrogen ion <> L-Cysteine + Sulfite + Thioredoxin disulfide + Acetic acid
o-acetyl-l-homoserine + Selenocysteine <> Selenocystathionine + Acetic acid
3-Hydroxy-5-oxohexanoate + Acetyl-CoA <> 3-Hydroxy-5-oxohexanoyl-CoA + Acetic acid
N-Acetyl-L-citrulline + Water <> Acetic acid + Citrulline
poly-&beta;-1,6-N-acetyl-D-glucosamine + Water Hydrogen ion + partially N-deacetylated poly-&beta;-1,6-N-acetyl-D-glucosamine + Acetic acid
a 2,3,4-saturated fatty acyl CoA + Acetic acid <> a fatty acid + Acetyl-CoA
Coenzyme A + Acetic acid + Adenosine triphosphate > Acetyl-CoA + Pyrophosphate + Adenosine monophosphate
Acetic acid + Adenosine triphosphate <> Acetylphosphate + ADP
Acetoacetic acid + Acetyl-CoA <> Acetoacetyl-CoA + Acetic acid
Water + an acetic ester > an alcohol + Acetic acid + Hydrogen ion
N-Acetylornithine + Water > Ornithine + Acetic acid
O-Acetylserine + Hydrogen sulfide <> Hydrogen ion + L-Cysteine + Acetic acid
Citric acid > Acetic acid + Oxalacetic acid
Water + N-Acetyl-D-Glucosamine 6-Phosphate > Glucosamine 6-phosphate + Acetic acid
Pyruvic acid + Water + a ubiquinone > Carbon dioxide + a ubiquinol + Acetic acid
Acetaldehyde + NADP + Water > Acetic acid + NADPH + Hydrogen ion
Acetic acid + Carbon dioxide + Hydrogen ion <> Pyruvic acid + Water
UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine + Water > UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine + Acetic acid
Adenosine triphosphate + Acetic acid > ADP + Acetylphosphate
Adenosine triphosphate + Acetic acid + CoA > Adenosine monophosphate + Pyrophosphate + Acetyl-CoA
N-Acetyl-D-galactosamine 6-phosphate + Water > D-Galactosamine 6-phosphate + Acetic acid
N-Acetylornithine + Water > Acetic acid + Ornithine
Acyl-CoA + Acetic acid > a fatty acid anion + Acetyl-CoA
Acyl-CoA + Acetic acid > a fatty acid anion + Acetyl-CoA
Citric acid > Acetic acid + Oxalacetic acid
Acetyl-CoA + Citric acid > Acetic acid + (3S)-Citryl-CoA
Adenosine triphosphate + Acetic acid + [citrate (pro-3S)-lyase](thiol form) > Adenosine monophosphate + Pyrophosphate + [citrate (pro-3S)-lyase](acetyl form)
Citric acid > Acetic acid + Oxalacetic acid
O-Acetylserine + Hydrogen sulfide > L-Cysteine + Acetic acid
O-Acetylserine + Hydrogen sulfide > L-Cysteine + Acetic acid
UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine + Water > UDP-3-O-(3-hydroxytetradecanoyl)-glucosamine + Acetic acid
N-Acetyl-D-Glucosamine 6-Phosphate + Water > D-glucosamine 6-phosphate + Acetic acid
Pyruvic acid + Ubiquinone-10 + Water > Acetic acid + Carbon dioxide + Ubiquinol-1
Adenosine triphosphate + Acetic acid > ADP + Acetylphosphate
Acyl-CoA + Acetic acid > a fatty acid anion + Acetyl-CoA
Acyl-CoA + Acetic acid <> Fatty acid anion + Acetyl-CoA
Acetyl-CoA + Citric acid <> Acetic acid + (3S)-Citryl-CoA
Adenosine triphosphate + Acetic acid + Citrate (pro-3S)-lyase (thiol form) <> Adenosine monophosphate + Pyrophosphate + Citrate (pro-3S)-lyase (acetyl form)
Acetyl-CoA + Oxalic acid <> Acetic acid + Oxalyl-CoA
Acetyl-CoA + 3-Hydroxy-5-oxohexanoate > Acetic acid + 3-Hydroxy-5-oxohexanoyl-CoA + 3-Hydroxy-5-oxohexanoyl-CoA
N-Acetylornithine + Water > Acetic acid + L-Ornithine monochlorohydrate/ornithine
N-Acetylornithine + Water > Ornithine + Acetic acid + Ornithine
O-Acetylserine > Hydrogen ion + Acetic acid + L-Cysteine
O-Acetylserine + Hydrogen sulfide > Hydrogen ion + Acetic acid + L-Cysteine
Hydrogen sulfide + O-Acetylserine <> L-Cysteine + Acetic acid + Hydrogen ion
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-α-D-glucosamine + Water > Acetic acid + UDP-3-O-(3-Hydroxytetradecanoyl)-D-glucosamine
N-Acetyl-D-Glucosamine 6-Phosphate + Water + N-Acetyl-D-Glucosamine 6-Phosphate > Acetic acid + Glucosamine 6-phosphate
O-Acetylserine + Thiosulfate + Thiosulfate > Cysteine-S-sulfate + Acetic acid
Diacetylchitobiose-6-phosphate + Water > N'-monoacetylchitobiose-6'-phosphate + Acetic acid
N-Acetyl-D-Glucosamine 6-Phosphate + Water > D-glucosamine 6-phosphate + Acetic acid
[a holo citrate lyase acyl-carrier protein] + Adenosine triphosphate + Acetic acid > Adenosine monophosphate + Pyrophosphate + an acetyl-[holo citrate lyase acyl-carrier protein]
Acetoacetic acid + Acetyl-CoA > Acetic acid + Acetoacetyl-CoA
Acetylphosphate + ADP > Adenosine triphosphate + Acetic acid
Acetic acid + Adenosine triphosphate + Coenzyme A > Pyrophosphate + Adenosine monophosphate + Acetyl-CoA
2 Pyruvic acid + 2 Water > Carbon dioxide + Acetic acid + Hydrogen ion + Electron
More...

SMPDB Pathways:
1,6-anhydro-<i>N</i>-acetylmuramic acid recyclingPW002064 Pw002064Pw002064 greyscalePw002064 simple
Acetate metabolismPW002090 Pw002090Pw002090 greyscalePw002090 simple
Amino sugar and nucleotide sugar metabolism IPW000886 Pw000886Pw000886 greyscalePw000886 simple
Amino sugar and nucleotide sugar metabolism IIPW000887 Pw000887Pw000887 greyscalePw000887 simple
Amino sugar and nucleotide sugar metabolism IIIPW000895 Pw000895Pw000895 greyscalePw000895 simple
Aminobenzoate DegradationPW000757 Pw000757Pw000757 greyscalePw000757 simple
Chitobiose DegradationPW002042 Pw002042Pw002042 greyscalePw002042 simple
Citrate lyase activationPW002075 Pw002075Pw002075 greyscalePw002075 simple
Galactose metabolismPW000821 Pw000821Pw000821 greyscalePw000821 simple
Lipopolysaccharide biosynthesisPW000831 Pw000831Pw000831 greyscalePw000831 simple
N-acetylneuraminate and N-acetylmannosamine and N-acetylglucosamine degradationPW002030 Pw002030Pw002030 greyscalePw002030 simple
Propanoate metabolismPW000940 Pw000940Pw000940 greyscalePw000940 simple
Secondary Metabolites: cysteine biosynthesis from serinePW000977 Pw000977Pw000977 greyscalePw000977 simple
Sulfur metabolismPW000922 Pw000922Pw000922 greyscalePw000922 simple
arginine metabolismPW000790 Pw000790Pw000790 greyscalePw000790 simple
cysteine biosynthesisPW000800 Pw000800Pw000800 greyscalePw000800 simple
lipopolysaccharide biosynthesis IIPW001905 Pw001905Pw001905 greyscalePw001905 simple
lipopolysaccharide biosynthesis IIIPW002059 Pw002059Pw002059 greyscalePw002059 simple
ornithine metabolismPW000791 Pw000791Pw000791 greyscalePw000791 simple
pyruvate to cytochrome bd terminal oxidase electron transferPW002087 Pw002087Pw002087 greyscalePw002087 simple
sulfur metabolism (butanesulfonate)PW000923 Pw000923Pw000923 greyscalePw000923 simple
sulfur metabolism (ethanesulfonate)PW000925 Pw000925Pw000925 greyscalePw000925 simple
sulfur metabolism (isethionate)PW000926 Pw000926Pw000926 greyscalePw000926 simple
sulfur metabolism (methanesulfonate)PW000927 Pw000927Pw000927 greyscalePw000927 simple
sulfur metabolism (propanesulfonate)PW000924 Pw000924Pw000924 greyscalePw000924 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
658± 25 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
Download Details
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9000000000-044b361cb9f5775c43feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01ox-9000000000-6437eb5f6a38c054dc37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-0505dfa8ee07a18a3ef3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0007-9000000000-a0d65dd4e056c1482aaaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-9000000000-a845ea0157abb3d7783bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-42ec023f024176a1c692View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-2bbab52cd9d076b89b2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-fb6d2f6298dd5bc37c2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-bc47c47ade16451259c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-01oy-9000000000-181ada67a3e5798d4419View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Camoutsis C, Trafalis D, Pairas G, Papageorgiou A: On the formation of 4-[N,N-bis(2-chloroethyl)amino]phenyl acetic acid esters of hecogenin and aza-homo-hecogenin and their antileukemic activity. Farmaco. 2005 Oct;60(10):826-9. Epub 2005 Aug 31. Pubmed: 16139280
  • Commodari F, Arnold DL, Sanctuary BC, Shoubridge EA: 1H NMR characterization of normal human cerebrospinal fluid and the detection of methylmalonic acid in a vitamin B12 deficient patient. NMR Biomed. 1991 Aug;4(4):192-200. Pubmed: 1931558
  • eMedicine: http://www.emedicinehealth.com/drug-acetic_acid_otic/article_em.htm
  • Fan DD, Luo Y, Mi Y, Ma XX, Shang L: Characteristics of fed-batch cultures of recombinant Escherichia coli containing human-like collagen cDNA at different specific growth rates. Biotechnol Lett. 2005 Jun;27(12):865-70. Pubmed: 16086249
  • Han, K., Lim, H. C., Hong, J. (1992). "Acetic acid formation in Escherichia coli fermentation." Biotechnol Bioeng 39:663-671. Pubmed: 18600996
  • 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. Pubmed: 22080510
  • 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. Pubmed: 21097882
  • Li M, Pan XL, Wang LL, Feng Y, Huang N, Wu Q, Li X, Wang BY: [Study of antmicrobial mechanisms of human cervical mucus: isolation and characterization of antibacterial polypeptides] Zhonghua Yi Xue Za Zhi. 2005 Apr 27;85(16):1109-12. Pubmed: 16029568
  • Muniz-Junqueira MI, Braga Lopes C, Magalhaes CA, Schleicher CC, Veiga JP: Acute and chronic influence of hemodialysis according to the membrane used on phagocytic function of neutrophils and monocytes and pro-inflammatory cytokines production in chronic renal failure patients. Life Sci. 2005 Nov 4;77(25):3141-55. Epub 2005 Jul 11. Pubmed: 16005905
  • Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. Pubmed: 7762816
  • 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. Pubmed: 12097436
  • Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. Pubmed: 15627241
  • Sugawara G, Nagino M, Nishio H, Ebata T, Takagi K, Asahara T, Nomoto K, Nimura Y: Perioperative synbiotic treatment to prevent postoperative infectious complications in biliary cancer surgery: a randomized controlled trial. Ann Surg. 2006 Nov;244(5):706-14. Pubmed: 17060763
  • Syrjanen K, Naud P, Derchain S, Roteli-Martins C, Longatto-Filho A, Tatti S, Branca M, Erzen M, Hammes LS, Matos J, Gontijo R, Sarian L, Braganca J, Arlindo FC, Maeda MY, Lorincz A, Dores GB, Costa S, Syrjanen S: Comparing PAP smear cytology, aided visual inspection, screening colposcopy, cervicography and HPV testing as optional screening tools in Latin America. Study design and baseline data of the LAMS study. Anticancer Res. 2005 Sep-Oct;25(5):3469-80. Pubmed: 16101165
  • Vaca G, Hernandez A, Ibarra B, Velazquez A, Olivares N, Sanchez-Corona J, Medina C, Cantu JM: Detection of inborn errors of metabolism in 1,117 patients studied because of suspected inherited disease. Arch Invest Med (Mex). 1981;12(3):341-8. Pubmed: 7294941
  • 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. Pubmed: 17765195
  • 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. Pubmed: 18331064
  • Yagi K, Nakamura A, Sekine A: [Magnification endoscopy diagnosis of Barrett's esophagus with methylene blue and acetic acid] Nippon Rinsho. 2005 Aug;63(8):1411-5. Pubmed: 16101231
  • Yri OE, Bjoro T, Fossa SD: Failure to achieve castration levels in patients using leuprolide acetate in locally advanced prostate cancer. Eur Urol. 2006 Jan;49(1):54-8; discussion 58. Epub 2005 Nov 15. Pubmed: 16314038
Synthesis Reference:Law, David John. Process for the preparation of carboxylic acids and/or derivatives thereof. PCT Int. Appl. (2007), 14pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15366
HMDB IDHMDB00042
Pubchem Compound ID176
Kegg IDC00033
ChemSpider ID171
WikipediaAcetic_acid
BioCyc IDACET
EcoCyc IDACET
Ligand ExpoCM

Enzymes

General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
metB
Uniprot ID:
P00935
Molecular weight:
41550
Reactions
O(4)-succinyl-L-homoserine + L-cysteine = L-cystathionine + succinate.
General function:
Involved in magnesium ion binding
Specific function:
Pyruvate + ferricytochrome b1 + H(2)O = acetate + CO(2) + ferrocytochrome b1
Gene Name:
poxB
Uniprot ID:
P07003
Molecular weight:
62011
Reactions
Pyruvate + ubiquinone + H(2)O = acetate + CO(2) + ubiquinol.
General function:
Involved in kinase activity
Specific function:
Involved in the activation of acetate to acetyl CoA and the secretion of acetate. During anaerobic growth of the organism, this enzyme is also involved in the synthesis of most of the ATP formed catabolically
Gene Name:
ackA
Uniprot ID:
P0A6A3
Molecular weight:
43290
Reactions
ATP + acetate = ADP + acetyl phosphate.
ATP + propanoate = ADP + propanoyl phosphate.
General function:
Involved in UDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylase activity
Specific function:
The key enzyme in the biosynthesis of lipid A, a phosphorylated glycolipid that anchors the lipopolysaccharide to the outer membrane of the cell. Degraded by FtsH; when the activity of FtsH is reduced too much lipid A and not enough phospholipids are made (both pathways use the same precursor), which is lethal
Gene Name:
lpxC
Uniprot ID:
P0A725
Molecular weight:
33956
Reactions
UDP-3-O-(3-hydroxytetradecanoyl)-N-acetylglucosamine + H(2)O = UDP-3-O-(3-hydroxytetradecanoyl)-glucosamine + acetate.
General function:
Involved in carbon-carbon lyase activity
Specific function:
Represents a citryl-ACP lyase
Gene Name:
citE
Uniprot ID:
P0A9I1
Molecular weight:
33109
Reactions
Citrate = acetate + oxaloacetate.
(3S)-citryl-CoA = acetyl-CoA + oxaloacetate.
General function:
Involved in acylphosphatase activity
Specific function:
An acylphosphate + H(2)O = a carboxylate + phosphate
Gene Name:
yccX
Uniprot ID:
P0AB65
Molecular weight:
10300
Reactions
An acylphosphate + H(2)O = a carboxylate + phosphate.
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate
Gene Name:
cysK
Uniprot ID:
P0ABK5
Molecular weight:
34489
Reactions
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate.
3-chloro-L-alanine + thioglycolate = S-carboxymethyl-L-cysteine + chloride.
General function:
Involved in hydrolase activity
Specific function:
N-acetyl-D-glucosamine 6-phosphate + H(2)O = D-glucosamine 6-phosphate + acetate
Gene Name:
nagA
Uniprot ID:
P0AF18
Molecular weight:
40949
Reactions
N-acetyl-D-glucosamine 6-phosphate + H(2)O = D-glucosamine 6-phosphate + acetate.
General function:
Involved in kinase activity
Specific function:
ATP + propanoate = ADP + propanoyl phosphate
Gene Name:
tdcD
Uniprot ID:
P11868
Molecular weight:
43384
Reactions
ATP + propanoate = ADP + propanoyl phosphate.
ATP + acetate = ADP + acetyl phosphate.
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
Two cysteine synthase enzymes are found. Both catalyze the same reaction. Cysteine synthase B can also use thiosulfate in place of sulfide to give cysteine thiosulfonate as a product
Gene Name:
cysM
Uniprot ID:
P16703
Molecular weight:
32664
Reactions
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate.
General function:
Involved in oxidoreductase activity
Specific function:
Involved in the breakdown of putrescine. Was previously shown to have a weak but measurable ALDH enzyme activity that prefers NADP over NAD as coenzyme
Gene Name:
puuC
Uniprot ID:
P23883
Molecular weight:
53418
Reactions
Gamma-glutamyl-gamma-aminobutyraldehyde + NAD(+) + H(2)O = gamma-glutamyl-gamma-aminobutyrate + NADH.
An aldehyde + NAD(P)(+) + H(2)O = a carboxylate + NAD(P)H.
General function:
Involved in zinc ion binding
Specific function:
Displays a broad specificity and can also deacylate substrates such as acetylarginine, acetylhistidine or acetylglutamate semialdehyde
Gene Name:
argE
Uniprot ID:
P23908
Molecular weight:
42347
Reactions
N(2)-acetyl-L-ornithine + H(2)O = acetate + L-ornithine.
General function:
Involved in acetate-CoA ligase activity
Specific function:
Enables the cell to use acetate during aerobic growth to generate energy via the TCA cycle, and biosynthetic compounds via the glyoxylate shunt. Acetylates CheY, the response regulator involved in flagellar movement and chemotaxis
Gene Name:
acs
Uniprot ID:
P27550
Molecular weight:
72093
Reactions
ATP + acetate + CoA = AMP + diphosphate + acetyl-CoA.
General function:
Involved in ATP binding
Specific function:
Catalyzes two reactions:the first one is the production of beta-formyl glycinamide ribonucleotide (GAR) from formate, ATP and beta GAR; the second, a side reaction, is the production of acetyl phosphate and ADP from acetate and ATP
Gene Name:
purT
Uniprot ID:
P33221
Molecular weight:
42433
Reactions
Formate + ATP + 5'-phospho-ribosylglycinamide = 5'-phosphoribosyl-N-formylglycinamide + ADP + diphosphate.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADP-dependent oxidation of diverse aldehydes such as chloroacetaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, mafosfamide, 4- hydroperoxycyclophosphamide. Its preferred substrates are acetaldehyde and chloroacetaldehyde
Gene Name:
aldB
Uniprot ID:
P37685
Molecular weight:
56306
General function:
Involved in hydrolase activity
Specific function:
N-acetyl-D-galactosamine 6-phosphate + H(2)O = D-galactosamine 6-phosphate + acetate
Gene Name:
agaA
Uniprot ID:
P42906
Molecular weight:
17519
Reactions
N-acetyl-D-galactosamine 6-phosphate + H(2)O = D-galactosamine 6-phosphate + acetate.
General function:
Energy production and conversion
Specific function:
Covalent carrier of the coenzyme of citrate lyase
Gene Name:
citD
Uniprot ID:
P69330
Molecular weight:
10689
General function:
Involved in citrate CoA-transferase activity
Specific function:
Represents a citrate:acetyl-ACP transferase
Gene Name:
citF
Uniprot ID:
P75726
Molecular weight:
55172
Reactions
Citrate = acetate + oxaloacetate.
Acetyl-CoA + citrate = acetate + (3S)-citryl-CoA.
General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoD
Uniprot ID:
P76458
Molecular weight:
23526
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.
General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoA
Uniprot ID:
P76459
Molecular weight:
22960
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.
General function:
Involved in [citrate (pro-3S)-lyase] ligase activity
Specific function:
Acetylation of prosthetic group (2-(5''-phosphoribosyl)- 3'-dephosphocoenzyme-A) of the gamma subunit of citrate lyase
Gene Name:
citC
Uniprot ID:
P77390
Molecular weight:
40077
Reactions
ATP + acetate + [citrate (pro-3S)-lyase](thiol form) = AMP + diphosphate + [citrate (pro-3S)-lyase](acetyl form).
General function:
Involved in prosthetic group biosynthetic process
Specific function:
Transfers 2-(5''-triphosphoribosyl)-3'- dephosphocoenzyme-A on a serine residue to the apo-acyl carrier protein (gamma chain) of the citrate lyase to yield holo-acyl carrier protein
Gene Name:
citX
Uniprot ID:
P0A6G5
Molecular weight:
20270
Reactions
2'-(5-triphosphoribosyl)-3'-dephospho-CoA + citrate lyase apo-[acyl-carrier-protein] = citrate lyase holo-[acyl-carrier-protein] + diphosphate.
General function:
Not Available
Specific function:
Not Available
Gene Name:
yjdM
Uniprot ID:
P0AFJ1
Molecular weight:
Not Available
General function:
polysaccharide catabolic process
Specific function:
ChbG is essential for growth on the acetylated chitooligosaccharides chitobiose and chitotriose but is dispensable for growth on cellobiose and chitosan dimer, the deacetylated form of chitobiose. Deacetylation of chitobiose-6-P and chitotriose-6-P is necessary for both the activation of the chb promoter by the regulatory protein ChbR and the hydrolysis of phosphorylated beta-glucosides by the phospho-beta-glucosidase ChbF. Catalyzes the removal of only one acetyl group from chitobiose-6-P to yield monoacetylchitobiose-6-P, the inducer of ChbR and the substrate of ChbF. It can also use chitobiose and chitotriose as substrates.
Gene Name:
chbG
Uniprot ID:
P37794
Molecular weight:
27773
Reactions
2-(acetylamino)-4-O-(2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranose + H(2)O = 2-(acetylamino)-4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranose + acetate

Transporters

General function:
Lipid transport and metabolism
Specific function:
Responsible for the intake of short-chain fatty acids
Gene Name:
atoE
Uniprot ID:
P76460
Molecular weight:
47527
General function:
Involved in transporter activity
Specific function:
Transports acetate
Gene Name:
actP
Uniprot ID:
B1XCV3
Molecular weight:
59197
General function:
Involved in transporter activity
Specific function:
Transports acetate
Gene Name:
actP
Uniprot ID:
C5A160
Molecular weight:
59197
General function:
Involved in transporter activity
Specific function:
Transports acetate. Also able to transport glycolate
Gene Name:
actP
Uniprot ID:
P32705
Molecular weight:
59197
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368