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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 19:05:03 UTC
HMDB IDHMDB0001043
Secondary Accession Numbers
  • HMDB01043
Metabolite Identification
Common NameArachidonic acid
DescriptionArachidonic acid is a polyunsaturated, essential fatty acid that has a 20-carbon chain as a backbone and four cis-double bonds at the C5, C8, C11, and C14 positions. 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 synthesized 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 into 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs), their corresponding dihydroxyeicosatrienoic 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
ValueSource
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acidChEBI
(5Z,8Z,11Z,14Z)-Icosatetraenoic acidChEBI
AAChEBI
all-cis-5,8,11,14-Eicosatetraenoic acidChEBI
ARAChEBI
ArachidonateChEBI
ArachidonsaeureChEBI
cis-5,8,11,14-Eicosatetraenoic acidChEBI
cis-Delta(5,8,11,14)-Eicosatetraenoic acidChEBI
(5Z,8Z,11Z,14Z)-5,8,11,14-IcosatetraenoateGenerator
(5Z,8Z,11Z,14Z)-IcosatetraenoateGenerator
all-cis-5,8,11,14-EicosatetraenoateGenerator
cis-5,8,11,14-EicosatetraenoateGenerator
cis-delta(5,8,11,14)-EicosatetraenoateGenerator
cis-δ(5,8,11,14)-eicosatetraenoateGenerator
cis-δ(5,8,11,14)-eicosatetraenoic acidGenerator
(all-Z)-5,8,11,14-EicosatetraenoateHMDB
(all-Z)-5,8,11,14-Eicosatetraenoic acidHMDB
5,8,11,14-all-cis-EicosatetraenoateHMDB
5,8,11,14-all-cis-Eicosatetraenoic acidHMDB
5,8,11,14-EicosatetraenoateHMDB
5,8,11,14-Eicosatetraenoic acidHMDB
5-cis,8-cis,11-cis,14-cis-EicosatetraenoateHMDB
5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acidHMDB
5Z,8Z,11Z,14Z-EicosatetraenoateHMDB
5Z,8Z,11Z,14Z-Eicosatetraenoic acidHMDB
cis-D5,8,11,14-EicosatetraenoateHMDB
cis-D5,8,11,14-Eicosatetraenoic acidHMDB
ImmunocytophyteHMDB
Arachidonate, sodiumMeSH
Arachidonic acid, (all-Z)-isomer, 3H-labeledMeSH
Arachidonic acid, ammonium salt, (all-Z)-isomerMeSH
Arachidonic acid, cerium salt, (all-Z)-isomerMeSH
Arachidonic acid, sodium saltMeSH
Arachidonic acid, sodium salt, (all-Z)-isomerMeSH
Vitamin FMeSH
Arachidonic acid, cesium salt, (all-Z)-isomerMeSH
Arachidonic acid, lithium salt, (all-Z)-isomerMeSH
Arachidonic acid, potassium salt, (all-Z)-isomerMeSH
Sodium arachidonateMeSH
Arachidonic acid, (all-Z)-isomer, 1-(14)C-labeledMeSH
Arachidonic acid, zinc salt, (all-Z)-isomerMeSH
FA(20:4(5Z,8Z,11Z,14Z))HMDB
Chemical FormulaC20H32O2
Average Molecular Weight304.4669
Monoisotopic Molecular Weight304.240230268
IUPAC Name(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Traditional 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
DescriptionThis compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.98SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.00015 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 Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.95 m³·mol⁻¹ChemAxon
Polarizability37.2 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-005c-9800000000-87c290971fc8a628fb23View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005c-9800000000-87c290971fc8a628fb23View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-6900000000-6870df266b6c73f2a4a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7390000000-7004b9cd28a9b3d9c991View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05i9-9252000000-475d13959ee8ce889646View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0nmi-0913000000-95846e8d5e8afd29664bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-6bd9d0477c122d3eed94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009000000-510ea33e558fa238a1d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0009000000-73a6b21464acba15463cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0009000000-4dd23c77f8e48c0ab9ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0049000000-102d050109d3c78b1a25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0a4i-0090000000-2fb9003e782ec3d05e20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0nmi-0913000000-95846e8d5e8afd29664bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009000000-6bd9d0477c122d3eed94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009000000-510ea33e558fa238a1d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0049000000-102d050109d3c78b1a25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1196000000-a42ea66033eb9771d36dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-5691000000-2bc7b1ae5487233dfce8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-7950000000-b15a8d382a4b3ad62d08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-28a9bbfed5fabd10c0c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2079000000-3f6e64ef7522a793e9a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9130000000-9c0c8bb5fc8e30bf53c7View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • 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
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.94 +/- 0.058 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified14 +/- 12 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified31.6 +/- 21.7 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified55.4 +/- 4.48 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified31.5 +/- 25.8 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified31.7 +/- 30.4 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified5.263 +/- 2.072 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified594.5 +/- 144.9 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected and Quantified348.150 +/- 52.551 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified344.865 +/- 55.835 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified312.0208 +/- 62.404 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified348.150 +/- 49.266 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified12 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified15 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified16 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified17 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified19 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified20 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified66 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified82 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified86 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified132 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified134 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified158 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified475.750 +/- 136.599 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified349.398 +/- 84.476 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified8.50 +/- 1.58 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified660 +/- 130 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified590 +/- 120 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.35 (0.03 - 0.66) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.45 +/- 1.63 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified34.3 +/- 27.8 uMAdult (>18 years old)BothHypertension details
BloodDetected and Quantified38.5 +/- 2.18 uMAdult (>18 years old)Both
Schizophrenia
details
BloodDetected and Quantified34.0 +/- 28.6 uMAdult (>18 years old)MaleEssential hypertension details
BloodDetected and Quantified34.9 +/- 26.4 uMAdult (>18 years old)FemaleEssential hypertension details
BloodDetected and Quantified415.6 +/- 114.3 uMAdult (>18 years old)Not Specified
Isovaleric acidemia
details
BloodDetected but not Quantified Adult (>18 years old)Both
Pancreatic ductal adenocarcinoma
details
BloodDetected and Quantified10.27 +/- 2.11 uMAdult (>18 years old)FemaleGestational diabetes mellitus (GDM) details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothIleal Crohn's disease details
FecesDetected but not Quantified Newborn (0-30 days old)Not Specified
Premature neonates
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)FemaleInterstitial cystitis details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Bladder infections
  1. Braundmeier-Fleming A, Russell NT, Yang W, Nas MY, Yaggie RE, Berry M, Bachrach L, Flury SC, Marko DS, Bushell CB, Welge ME, White BA, Schaeffer AJ, Klumpp DJ: Stool-based biomarkers of interstitial cystitis/bladder pain syndrome. Sci Rep. 2016 May 18;6:26083. doi: 10.1038/srep26083. [PubMed:27188581 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Essential hypertension
  1. 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. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Schizophrenia
  1. Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ]
Gestational diabetes
  1. 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
  1. 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. doi: 10.1291/hypres.31.623. [PubMed:18633173 ]
Isovaleric acidemia
  1. Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011872
KNApSAcK IDC00000388
Chemspider ID392692
KEGG Compound IDC00219
BioCyc IDARACHIDONIC_ACID
BiGG ID1586189
Wikipedia LinkArachidonic_acid
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)Download (PDF)
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. doi: 10.1038/nature07762. [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 10 proteins. There are 115 proteins in total.

Enzymes

General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
P49327
Molecular weight:
273424.06
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
General function:
Involved in sugar binding
Specific function:
Has lysophospholipase activity.
Gene Name:
LGALS13
Uniprot ID:
Q9UHV8
Molecular weight:
16118.44
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Molecular weight:
21066.99
Reactions
Phosphatidylcholine + Water → 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic aciddetails

Transporters

General function:
Lipid transport and metabolism
Specific function:
Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:
SLC27A1
Uniprot ID:
Q6PCB7
Molecular weight:
71107.5
General function:
Not Available
Specific function:
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, as well as PGE1, PGE2 and PGF2A
Gene Name:
SLCO2A1
Uniprot ID:
Q92959
Molecular weight:
70117.0
References
  1. Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL: Identification and characterization of a prostaglandin transporter. Science. 1995 May 12;268(5212):866-9. [PubMed:7754369 ]

Only showing the first 10 proteins. There are 115 proteins in total.