Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:30:09 UTC
HMDB IDHMDB01043
Secondary Accession NumbersNone
Metabolite Identification
Common NameArachidonic acid
DescriptionArachidonic acid is a polyunsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid. Arachidonic acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids. Arachidonic acid in cell membrane phospholipids is the substrate for the synthesis of a range of biologically active compounds (eicosanoids) including prostaglandins, thromboxanes, and leukotrienes. These compounds can act as mediators in their own right and can also act as regulators of other processes, such as platelet aggregation, blood clotting, smooth muscle contraction, leukocyte chemotaxis, inflammatory cytokine production, and immune function. Arachidonic acid can be metabolized by cytochrome p450 (CYP450) enzymes to 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs), their corresponding dihydroxyeicosa-trienoic acids (DHETs), and 20-hydroxyeicosatetraenoic acid (20-HETE). The production of kidney CYP450 arachidonic acid metabolites is altered in diabetes, pregnancy, hepatorenal syndrome, and in various models of hypertension, and it is likely that changes in this system contribute to the abnormalities in renal function that are associated with many of these conditions. Phospholipase A2 (PLA2) catalyzes the hydrolysis of the sn-2 position of membrane glycerophospholipids to liberate arachidonic acid (PMID: 12736897 , 12736897 , 12700820 , 12570747 , 12432908 ).
Structure
Thumb
Synonyms
  1. (all-Z)-5,8,11,14-Eicosatetraenoate
  2. (all-Z)-5,8,11,14-Eicosatetraenoic acid
  3. 5,8,11,14-All-cis-Eicosatetraenoate
  4. 5,8,11,14-All-cis-Eicosatetraenoic acid
  5. 5,8,11,14-Eicosatetraenoate
  6. 5,8,11,14-Eicosatetraenoic acid
  7. 5-cis,8-cis,11-cis,14-cis-Eicosatetraenoate
  8. 5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acid
  9. 5Z,8Z,11Z,14Z-Eicosatetraenoate
  10. 5Z,8Z,11Z,14Z-Eicosatetraenoic acid
  11. All-cis-5,8,11,14-Eicosatetraenoate
  12. All-cis-5,8,11,14-Eicosatetraenoic acid
  13. Arachidonic acid
  14. cis-D5,8,11,14-Eicosatetraenoate
  15. cis-D5,8,11,14-Eicosatetraenoic acid
  16. Immunocytophyte
Chemical FormulaC20H32O2
Average Molecular Weight304.4669
Monoisotopic Molecular Weight304.240230268
IUPAC Name(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Traditional IUPAC Namearachidonic acid
CAS Registry Number506-32-1
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
InChI KeyYZXBAPSDXZZRGB-DOFZRALJSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acids and Conjugates
Sub ClassUnsaturated Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Polyunsaturated fatty acids(KEGG)
  • Straight Chain Fatty Acids
  • Unsaturated fatty acids(KEGG)
  • Unsaturated fatty acids(Lipidmaps)
  • eicosa-5,8,11,14-tetraenoic acid(ChEBI)
  • eicosanoid(ChEBI)
  • omega-6 fatty acid(ChEBI)
  • very long-chain fatty acid(ChEBI)
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
Direct ParentUnsaturated Fatty Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Prostaglandin and leukotriene metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.98SANGSTER (1993)
Predicted Properties
PropertyValueSource
water solubility1.510E-04 g/LALOGPS
logP6.8ALOGPS
logP6.59ChemAxon
logS-6.3ALOGPS
pKa (strongest acidic)4.82ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.3ChemAxon
rotatable bond count14ChemAxon
refractivity99.95ChemAxon
polarizability37.2ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Lung
  • Muscle
  • Myelin
  • Nerve Cells
  • Nervous Tissues
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testes
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018map00592
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified2.94 +/- 0.058 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified14 +/- 12 uMAdult (>18 years old)Not SpecifiedNormal
BloodDetected and Quantified31.6 +/- 21.7 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified31.5 +/- 25.8 uMAdult (>18 years old)MaleNormal
BloodDetected and Quantified31.7 +/- 30.4 uMAdult (>18 years old)FemaleNormal
BloodDetected and Quantified5.263 +/- 2.072 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified8.50 +/- 1.58 uMAdult (>18 years old)FemaleNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.35 (0.03 - 0.66) uMAdult (>18 years old)Not SpecifiedNormal
UrineDetected and Quantified2.45 +/- 1.63 umol/mmol creatinineAdult (>18 years old)FemaleNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified34.3 +/- 27.8 uMAdult (>18 years old)BothHypertension
BloodDetected and Quantified34.0 +/- 28.6 uMAdult (>18 years old)MaleEssential hypertension
BloodDetected and Quantified34.9 +/- 26.4 uMAdult (>18 years old)FemaleEssential hypertension
BloodDetected and Quantified10.27 +/- 2.11 uMAdult (>18 years old)FemaleGestational diabetes mellitus (GDM)
Associated Disorders and Diseases
Disease References
Essential hypertension
  • Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. Pubmed: 18633173
Gestational diabetes
  • Min Y, Ghebremeskel K, Lowy C, Thomas B, Crawford MA: Adverse effect of obesity on red cell membrane arachidonic and docosahexaenoic acids in gestational diabetes. Diabetologia. 2004 Jan;47(1):75-81. Epub 2003 Nov 22. Pubmed: 14634727
Hypertension
  • Wang S, Ma A, Song S, Quan Q, Zhao X, Zheng X: Fasting serum free fatty acid composition, waist/hip ratio and insulin activity in essential hypertensive patients. Hypertens Res. 2008 Apr;31(4):623-32. Pubmed: 18633173
Associated OMIM IDs
DrugBank IDDB04557
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011872
KNApSAcK IDC00000388
Chemspider ID392692
KEGG Compound IDC00219
BioCyc IDARACHIDONIC_ACID
BiGG ID1586189
Wikipedia LinkArachidonic acid
NuGOwiki LinkHMDB01043
Metagene LinkHMDB01043
METLIN ID193
PubChem Compound444899
PDB IDACD
ChEBI ID15843
References
Synthesis ReferenceDai, Chuanchao; Yuan, Zhilin; Wang, Anqi. Production of arachidonic acid and eicosapentaenoic acid with organic wastewater of soybean products. Zhongguo Youzhi (2004), 29(5), 31-33.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  2. Markuszewski L, Rosiak M, Golanski J, Rysz J, Spychalska M, Watala C: Reduced blood platelet sensitivity to aspirin in coronary artery disease: are dyslipidaemia and inflammatory states possible factors predisposing to sub-optimal platelet response to aspirin? Basic Clin Pharmacol Toxicol. 2006 May;98(5):503-9. Pubmed: 16635110
  3. Frelinger AL 3rd, Furman MI, Linden MD, Li Y, Fox ML, Barnard MR, Michelson AD: Residual arachidonic acid-induced platelet activation via an adenosine diphosphate-dependent but cyclooxygenase-1- and cyclooxygenase-2-independent pathway: a 700-patient study of aspirin resistance. Circulation. 2006 Jun 27;113(25):2888-96. Epub 2006 Jun 19. Pubmed: 16785341
  4. Daskalou T, Karamouzis M, Liaros G: [Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques] Hell J Nucl Med. 2006 Jan-Apr;9(1):49-52. Pubmed: 16617398
  5. Sacerdoti D, Gatta A, McGiff JC: Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology. Prostaglandins Other Lipid Mediat. 2003 Oct;72(1-2):51-71. Pubmed: 14626496
  6. Claria J, Arroyo V: Prostaglandins and other cyclooxygenase-dependent arachidonic acid metabolites and the kidney in liver disease. Prostaglandins Other Lipid Mediat. 2003 Oct;72(1-2):19-33. Pubmed: 14626494
  7. Pantaleo P, Marra F, Vizzutti F, Spadoni S, Ciabattoni G, Galli C, La Villa G, Gentilini P, Laffi G: Effects of dietary supplementation with arachidonic acid on platelet and renal function in patients with cirrhosis. Clin Sci (Lond). 2004 Jan;106(1):27-34. Pubmed: 12877651
  8. Hughes-Fulford M, Tjandrawinata RR, Li CF, Sayyah S: Arachidonic acid, an omega-6 fatty acid, induces cytoplasmic phospholipase A2 in prostate carcinoma cells. Carcinogenesis. 2005 Sep;26(9):1520-6. Epub 2005 May 5. Pubmed: 15878913
  9. Kudolo GB, Wang W, Barrientos J, Elrod R, Blodgett J: The ingestion of Ginkgo biloba extract (EGb 761) inhibits arachidonic acid-mediated platelet aggregation and thromboxane B2 production in healthy volunteers. J Herb Pharmacother. 2004;4(4):13-26. Pubmed: 15927922
  10. Burke J, Kraft WK, Greenberg HE, Gleave M, Pitari GM, VanBuren S, Wagner JA, Waldman SA: Relationship of arachidonic acid concentration to cyclooxygenase-dependent human platelet aggregation. J Clin Pharmacol. 2003 Sep;43(9):983-9. Pubmed: 12971030
  11. Carroll RC, Craft RM, Chavez JJ, Snider CC, Bresee SJ, Cohen E: A Thrombelastograph whole blood assay for clinical monitoring of NSAID-insensitive transcellular platelet activation by arachidonic acid. J Lab Clin Med. 2005 Jul;146(1):30-5. Pubmed: 16025089
  12. Cuisset T, Frere C, Quilici J, Barbou F, Morange PE, Hovasse T, Bonnet JL, Alessi MC: High post-treatment platelet reactivity identified low-responders to dual antiplatelet therapy at increased risk of recurrent cardiovascular events after stenting for acute coronary syndrome. J Thromb Haemost. 2006 Mar;4(3):542-9. Epub 2005 Dec 22. Pubmed: 16371119
  13. Arruzazabala ML, Mas R, Molina V, Carbajal D, Fernandez L, Illnait J, Castano G, Fernandez J, Mendoza S: Effects of d-003, a new substance purified from sugar cane wax, on platelet aggregation and plasma levels of arachidonic acid metabolites in healthy volunteers. Int J Clin Pharmacol Res. 2004;24(2-3):55-63. Pubmed: 15689052
  14. Sinzinger H: Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques. Hell J Nucl Med. 2006 May-Aug;9(2):111; author reply 111-2. Pubmed: 16894418
  15. Bringmann A, Schopf S, Faude F, Reichenbach A: Arachidonic acid-induced inhibition of Ca2+ channel currents in retinal glial (Muller) cells. Graefes Arch Clin Exp Ophthalmol. 2001 Nov;239(11):859-64. Pubmed: 11789867
  16. Eikelboom JW, Hankey GJ, Thom J, Claxton A, Yi Q, Gilmore G, Staton J, Barden A, Norman PE: Enhanced antiplatelet effect of clopidogrel in patients whose platelets are least inhibited by aspirin: a randomized crossover trial. J Thromb Haemost. 2005 Dec;3(12):2649-55. Pubmed: 16359503
  17. Cox D, Maree AO, Dooley M, Conroy R, Byrne MF, Fitzgerald DJ: Effect of enteric coating on antiplatelet activity of low-dose aspirin in healthy volunteers. Stroke. 2006 Aug;37(8):2153-8. Epub 2006 Jun 22. Pubmed: 16794200
  18. Yamada N, Miyamoto M, Isogaya M, Suzuki M, Ikezawa S, Ohno M, Otake A, Umemura K: TRA-418, a novel compound having both thromboxane A(2) receptor antagonistic and prostaglandin I(2) receptor agonistic activities: its antiplatelet effects in human and animal platelets. J Thromb Haemost. 2003 Aug;1(8):1813-9. Pubmed: 12911598
  19. Payne DA, Jones CI, Hayes PD, Webster SE, Ross Naylor A, Goodall AH: Platelet inhibition by aspirin is diminished in patients during carotid surgery: a form of transient aspirin resistance? Thromb Haemost. 2004 Jul;92(1):89-96. Pubmed: 15213849
  20. Kroetz DL, Xu F: Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation. Annu Rev Pharmacol Toxicol. 2005;45:413-38. Pubmed: 15822183
  21. Pompeia C, Lima T, Curi R: Arachidonic acid cytotoxicity: can arachidonic acid be a physiological mediator of cell death? Cell Biochem Funct. 2003 Jun;21(2):97-104. Pubmed: 12736897
  22. Calder PC: Long-chain n-3 fatty acids and inflammation: potential application in surgical and trauma patients. Braz J Med Biol Res. 2003 Apr;36(4):433-46. Epub 2003 Apr 8. Pubmed: 12700820
  23. Zhao X, Imig JD: Kidney CYP450 enzymes: biological actions beyond drug metabolism. Curr Drug Metab. 2003 Feb;4(1):73-84. Pubmed: 12570747
  24. Kudo I, Murakami M: Phospholipase A2 enzymes. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:3-58. Pubmed: 12432908

Only showing the first 50 proteins. There are 115 proteins in total.

Enzymes

Gene Name:
FASN
Uniprot ID:
P49327
Gene Name:
PLA2G5
Uniprot ID:
P39877
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
PLA2G10
Uniprot ID:
O15496
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
LGALS13
Uniprot ID:
Q9UHV8
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
PLA2G6
Uniprot ID:
O60733
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
CLC
Uniprot ID:
Q05315
Gene Name:
PLA2G2A
Uniprot ID:
P14555
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
PNLIP
Uniprot ID:
P16233
Gene Name:
LIPC
Uniprot ID:
P11150
Gene Name:
LIPF
Uniprot ID:
P07098
Gene Name:
LIPG
Uniprot ID:
Q9Y5X9
Gene Name:
CEL
Uniprot ID:
P19835
Gene Name:
PNLIPRP2
Uniprot ID:
P54317
Gene Name:
LPL
Uniprot ID:
P06858
Gene Name:
CYP4A11
Uniprot ID:
Q02928
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion unknown 20-Hydroxyeicosatetraenoic acid + NADP + Waterdetails
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion unknown 11,12-EpETrE + NADP + Waterdetails
Gene Name:
CES1
Uniprot ID:
P23141
Gene Name:
CES2
Uniprot ID:
O00748
Gene Name:
BCHE
Uniprot ID:
P06276
Gene Name:
PLA2G4C
Uniprot ID:
Q9UP65
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
LIPE
Uniprot ID:
Q05469
Gene Name:
PLA2G3
Uniprot ID:
Q9NZ20
Reactions
Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
Gene Name:
ACYP2
Uniprot ID:
P14621
Gene Name:
ACYP1
Uniprot ID:
P07311
Gene Name:
ACY1
Uniprot ID:
Q03154
Gene Name:
ASPA
Uniprot ID:
P45381
Gene Name:
ACY3
Uniprot ID:
Q96HD9
Gene Name:
ALOX5
Uniprot ID:
P09917
Reactions
Arachidonic acid + Oxygen unknown leukotriene A(4) + Waterdetails
Arachidonic acid + Oxygen unknown 5(S)-Hydroperoxyeicosatetraenoic aciddetails
Arachidonic acid + Oxygen unknown Leukotriene A4 + Waterdetails
Gene Name:
ALOX15B
Uniprot ID:
O15296
Reactions
Arachidonic acid + Oxygen unknown 15(S)-HPETEdetails
Arachidonic acid + Oxygen unknown 8(S)-HPETEdetails
Gene Name:
ALOX12
Uniprot ID:
P18054
Reactions
Arachidonic acid + Oxygen unknown 12(S)-HPETEdetails
Gene Name:
PTGS2
Uniprot ID:
P35354
Reactions
Arachidonic acid + AH(2) + Oxygen unknown prostaglandin H(2) + A + Waterdetails
Arachidonic acid + Oxygen unknown Prostaglandin G2details
Gene Name:
PTGS1
Uniprot ID:
P23219
Reactions
Arachidonic acid + AH(2) + Oxygen unknown prostaglandin H(2) + A + Waterdetails
Arachidonic acid + Oxygen unknown Prostaglandin G2details
Gene Name:
ALOX15
Uniprot ID:
P16050
Reactions
Arachidonic acid + Oxygen unknown 15(S)-HPETEdetails
Gene Name:
CYP4F2
Uniprot ID:
P78329
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion unknown 20-Hydroxyeicosatetraenoic acid + NADP + Waterdetails
Gene Name:
CYP4F3
Uniprot ID:
Q08477
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion unknown 20-Hydroxyeicosatetraenoic acid + NADP + Waterdetails
Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
ACOT7
Uniprot ID:
O00154
Reactions
Arachidonyl-CoA + Water unknown Coenzyme A + Arachidonic aciddetails
Gene Name:
ACOT2
Uniprot ID:
P49753
Reactions
Arachidonyl-CoA + Water unknown Coenzyme A + Arachidonic aciddetails
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Reactions
Arachidonyl-CoA + Water unknown Coenzyme A + Arachidonic aciddetails

Transporters

Only showing the first 50 proteins. There are 115 proteins in total.