Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-15 18:56:53 UTC
HMDB IDHMDB00042
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetic acid
DescriptionAcetic acid is one of the simplest carboxylic acids. It is an important chemical reagent and industrial chemical that is used in the production of plastic soft drink bottles, photographic film; and polyvinyl acetate for wood glue, as well as many synthetic fibres and fabrics. In households diluted acetic acid is often used as a cleaning agent. In the food industry acetic acid is used as an acidity regulator. The acetyl group, derived from acetic acid, is fundamental to the biochemistry of virtually all forms of life. When bound to coenzyme A it 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. Acetic acid is also a component of the vaginal lubrication of humans and other primates, where it appears to serve as a mild antibacterial agent.
Structure
Thumb
Synonyms
  1. Acetate
  2. Ethanoate
  3. Ethanoic acid
  4. Ethylate
  5. Ethylic acid
  6. Glacial acetate
  7. Glacial acetic acid
  8. Kyselina octova
  9. Methanecarboxylate
  10. Methanecarboxylic acid
  11. Vinegar
  12. Vinegar acid
Chemical FormulaC2H4O2
Average Molecular Weight60.052
Monoisotopic Molecular Weight60.021129372
IUPAC Nameacetic acid
Traditional IUPAC Nameacetic acid
CAS Registry Number64-19-7
SMILES
CC(O)=O
InChI Identifier
InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
InChI KeyQTBSBXVTEAMEQO-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
Sub ClassCarboxylic Acid Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Saturated fatty acids(KEGG)
  • Straight chain fatty acids(KEGG)
  • Straight chain fatty acids(Lipidmaps)
  • monocarboxylic acid(ChEBI)
Substituents
  • N/A
Direct ParentCarboxylic Acids
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Microbial
Biofunction
  • Component of Glycerophospholipid metabolism
  • Component of Propanoate metabolism
  • Component of Pyruvate metabolism
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Golgi apparatus
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point16.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogP-0.17HANSCH,C ET AL. (1995)
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 area37.3ChemAxon
rotatable bond count0ChemAxon
refractivity12.64ChemAxon
polarizability5.34ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Golgi apparatus
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Kidney
  • Liver
  • Most Tissues
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045map00520
Ethanol DegradationSMP00449Not Available
Fatty Acid BiosynthesisSMP00456Not Available
Pyruvate MetabolismSMP00060map00620
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified30.4 (22.0-40.0) uMAdult (>18 years old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified41.9 +/- 15.1 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified116.0 +/- 55.0 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified58.0 +/- 27.0 uMNot SpecifiedBothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified100.0 +/- 30.0 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified284.0 +/- 126.0 uMChildren (1-13 year old)BothNormal
SalivaDetected and Quantified433 (19-2749) uMAdult (>18 years old)MaleCommentnormal
SalivaDetected and Quantified112 (5-726) uMAdult (>18 years old)MaleCommentnormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal
UrineDetected and Quantified13.0 (2.5-106.0) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified3.31 umol/mmol creatinineAdult (>18 years old)MaleNormal
  • Shaykhutdino...
UrineDetected and Quantified45.33 +/- 53.33 umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified42.2 +/- 17.3 uMAdult (>18 years old)Not SpecifiedHeart Transplant
Cerebrospinal Fluid (CSF)Detected and Quantified35.3 - 211.7 uMAdult (>18 years old)Not SpecifiedMultiple sclerosis
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer
UrineDetected and Quantified53.0 +/- 71.0 umol/mmol creatinineNot SpecifiedBothLung cancer
UrineDetected and Quantified23.7 +/- 4.5 umol/mmol creatinineAdult (>18 years old)Both3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency
UrineDetected and Quantified12.9 +/- 0 umol/mmol creatinineAdult (>18 years old)Both3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency
UrineDetected and Quantified54.1 +/- 23.8 umol/mmol creatinineAdult (>18 years old)BothArginosuccinic aciduria
UrineDetected and Quantified20.2 +/- 3.9 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia
UrineDetected and Quantified20.8 +/- 3 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia
UrineDetected and Quantified99.4 +/- 8.6 umol/mmol creatinineAdult (>18 years old)BothTyrosinemia I
UrineDetected and Quantified16.3 +/- 7.1 umol/mmol creatinineAdult (>18 years old)BothPhenylketonuria
UrineDetected and Quantified375.3 +/- 6.3 umol/mmol creatinineAdult (>18 years old)BothPhenylketonuria
UrineDetected and Quantified13.2 +/- 5.5 umol/mmol creatinineAdult (>18 years old)BothMaple syrup urine disease
UrineDetected and Quantified21.8 +/- 0 umol/mmol creatinineAdult (>18 years old)BothAminoaciduria
Associated Disorders and Diseases
Disease References
Lung Cancer
  • Stretch C, Eastman T, Mandal R, Eisner R, Wishart DS, Mourtzakis M, Prado CM, Damaraju S, Ball RO, Greiner R, Baracos VE: Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach. J Nutr. 2012 Jan;142(1):14-21. doi: 10.3945/jn.111.147751. Epub 2011 Dec 7. Pubmed: 22157537
Multiple sclerosis
  • Lutz NW, Viola A, Malikova I, Confort-Gouny S, Audoin B, Ranjeva JP, Pelletier J, Cozzone PJ: Inflammatory multiple-sclerosis plaques generate characteristic metabolic profiles in cerebrospinal fluid. PLoS ONE. 2007 Jul 4;2(7):e595. Pubmed: 17611627
Associated OMIM IDs
DrugBank IDDB03166
DrugBank Metabolite IDDBMET00484
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008299
KNApSAcK IDC00001176
Chemspider ID171
KEGG Compound IDC00033
BioCyc IDACET
BiGG ID33590
Wikipedia LinkAcetic acid
NuGOwiki LinkHMDB00042
Metagene LinkHMDB00042
METLIN ID3206
PubChem Compound176
PDB IDACY
ChEBI ID15366
References
Synthesis ReferenceLaw, David John. Process for the preparation of carboxylic acids and/or derivatives thereof. PCT Int. Appl. (2007), 14pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. eMedicine

Enzymes

Gene Name:
HMGCL
Uniprot ID:
P35914
Reactions
3-Hydroxy-3-(4-methylpent-3-en-1-yl)glutaryl-CoA unknown 7-Methyl-3-oxo-6-octenoyl-CoA + Acetic aciddetails
Gene Name:
ACOT12
Uniprot ID:
Q8WYK0
Reactions
Acetyl-CoA + Water unknown Coenzyme A + Acetic aciddetails
Gene Name:
ACSS2
Uniprot ID:
Q9NR19
Reactions
Adenosine triphosphate + Acetic acid + Coenzyme A unknown Adenosine monophosphate + Pyrophosphate + Acetyl-CoAdetails
Adenosine triphosphate + Acetic acid unknown Pyrophosphate + Acetyl adenylatedetails
Gene Name:
ACSS1
Uniprot ID:
Q9NUB1
Reactions
Adenosine triphosphate + Acetic acid + Coenzyme A unknown Adenosine monophosphate + Pyrophosphate + Acetyl-CoAdetails
Adenosine triphosphate + Acetic acid unknown Pyrophosphate + Acetyl adenylatedetails
Gene Name:
PON3
Uniprot ID:
Q15166
Reactions
A phenyl acetate + Water unknown a phenol + Acetic aciddetails
4-Hydroxyphenyl acetate + Water unknown Hydroquinone + Acetic aciddetails
Gene Name:
PON1
Uniprot ID:
P27169
Reactions
A phenyl acetate + Water unknown a phenol + Acetic aciddetails
4-Hydroxyphenyl acetate + Water unknown Hydroquinone + Acetic aciddetails
Gene Name:
PON2
Uniprot ID:
Q15165
Reactions
A phenyl acetate + Water unknown a phenol + Acetic aciddetails
4-Hydroxyphenyl acetate + Water unknown Hydroquinone + Acetic aciddetails
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Reactions
Acetaldehyde + NAD + Water unknown Acetic acid + NADH + Hydrogen Iondetails
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Reactions
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Iondetails
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Reactions
Acetaldehyde + NAD + Water unknown Acetic acid + NADH + Hydrogen Iondetails
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Reactions
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Iondetails
Gene Name:
ALDH2
Uniprot ID:
P05091
Reactions
Acetaldehyde + NAD + Water unknown Acetic acid + NADH + Hydrogen Iondetails
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Iondetails
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Reactions
Acetaldehyde + NAD + Water unknown Acetic acid + NADH + Hydrogen Iondetails
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Iondetails
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Reactions
Acetaldehyde + NAD + Water unknown Acetic acid + NADH + Hydrogen Iondetails
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Iondetails
Gene Name:
CES1
Uniprot ID:
P23141
Reactions
4-Methylumbelliferyl acetate + Water unknown 4-Methylumbelliferone + Acetic aciddetails
Gene Name:
CES2
Uniprot ID:
O00748
Reactions
4-Methylumbelliferyl acetate + Water unknown 4-Methylumbelliferone + Acetic aciddetails
Gene Name:
ESD
Uniprot ID:
P10768
Reactions
4-Methylumbelliferyl acetate + Water unknown 4-Methylumbelliferone + Acetic aciddetails
Gene Name:
PLA2G7
Uniprot ID:
Q13093
Reactions
1-alkyl-2-acetyl-sn-glycero-3-phosphocholine + Water unknown 1-alkyl-sn-glycero-3-phosphocholine + Acetic aciddetails
2-Acetyl-1-alkyl-sn-glycero-3-phosphocholine + Water unknown 1-Organyl-2-lyso-sn-glycero-3-phosphocholine + Acetic aciddetails
Gene Name:
ACHE
Uniprot ID:
P22303
Reactions
Acetylcholine + Water unknown Choline + Acetic aciddetails
Gene Name:
PAFAH1B3
Uniprot ID:
Q15102
Reactions
1-alkyl-2-acetyl-sn-glycero-3-phosphocholine + Water unknown 1-alkyl-sn-glycero-3-phosphocholine + Acetic aciddetails
2-Acetyl-1-alkyl-sn-glycero-3-phosphocholine + Water unknown 1-Organyl-2-lyso-sn-glycero-3-phosphocholine + Acetic aciddetails
Gene Name:
PAFAH1B2
Uniprot ID:
P68402
Reactions
1-alkyl-2-acetyl-sn-glycero-3-phosphocholine + Water unknown 1-alkyl-sn-glycero-3-phosphocholine + Acetic aciddetails
2-Acetyl-1-alkyl-sn-glycero-3-phosphocholine + Water unknown 1-Organyl-2-lyso-sn-glycero-3-phosphocholine + Acetic aciddetails
Gene Name:
PAFAH2
Uniprot ID:
Q99487
Reactions
1-alkyl-2-acetyl-sn-glycero-3-phosphocholine + Water unknown 1-alkyl-sn-glycero-3-phosphocholine + Acetic aciddetails
2-Acetyl-1-alkyl-sn-glycero-3-phosphocholine + Water unknown 1-Organyl-2-lyso-sn-glycero-3-phosphocholine + Acetic aciddetails
Gene Name:
SIAE
Uniprot ID:
Q9HAT2
Reactions
N-acetyl-O-acetylneuraminate + Water unknown N-Acetylneuraminic acid + Acetic aciddetails
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Reactions
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Iondetails
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Reactions
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Iondetails
Gene Name:
ACYP2
Uniprot ID:
P14621
Reactions
Acetylphosphate + Water unknown Acetic acid + Phosphoric aciddetails
Gene Name:
ACYP1
Uniprot ID:
P07311
Reactions
Acetylphosphate + Water unknown Acetic acid + Phosphoric aciddetails
Gene Name:
ACY1
Uniprot ID:
Q03154
Reactions
N-Acetylornithine + Water unknown Acetic acid + Ornithinedetails
Gene Name:
ASPA
Uniprot ID:
P45381
Reactions
N-Acetyl-L-aspartic acid + Water unknown Acetic acid + L-Aspartic aciddetails
Gene Name:
PIGL
Uniprot ID:
Q9Y2B2
Reactions
6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + Water unknown 6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + Acetic aciddetails
+ Water unknown + Acetic aciddetails
Gene Name:
ACY3
Uniprot ID:
Q96HD9
Reactions
N-Acetyl-L-aspartic acid + Water unknown Acetic acid + L-Aspartic aciddetails
Gene Name:
CYP17A1
Uniprot ID:
P05093
Reactions
17a-Hydroxypregnenolone + Reduced acceptor + Oxygen unknown Dehydroepiandrosterone + Acetic acid + Acceptor + Waterdetails
17-Hydroxyprogesterone + Reduced acceptor + Oxygen unknown Androstenedione + Acetic acid + Acceptor + Waterdetails
Gene Name:
AMDHD2
Uniprot ID:
Q9Y303
Reactions
N-Acetyl-D-Glucosamine 6-Phosphate + Water unknown Glucosamine 6-phosphate + Acetic aciddetails
Gene Name:
ASPG
Uniprot ID:
Q86U10
Reactions
1-alkyl-2-acetyl-sn-glycero-3-phosphocholine + Water unknown 1-alkyl-sn-glycero-3-phosphocholine + Acetic aciddetails
Gene Name:
ACSS2
Uniprot ID:
Q96FY7
Gene Name:
ACSS3
Uniprot ID:
Q9H6R3
Reactions
Adenosine triphosphate + Acetic acid + Coenzyme A unknown Adenosine monophosphate + Pyrophosphate + Acetyl-CoAdetails

Transporters

Gene Name:
SLC16A1
Uniprot ID:
P53985