Human Metabolome Database Version 3.5

Showing metabocard for Arachidonic acid (HMDB01043)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:09 -0600
HMDB ID HMDB01043
Secondary Accession Numbers None
Metabolite Identification
Common Name Arachidonic acid
Description Arachidonic 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 Link_out, 12736897 Link_out, 12700820 Link_out, 12570747 Link_out, 12432908 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C20H32O2
Average Molecular Weight 304.4669
Monoisotopic Molecular Weight 304.240230268
IUPAC Name (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Traditional IUPAC Name arachidonic acid
CAS Registry Number 506-32-1
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 Key YZXBAPSDXZZRGB-DOFZRALJSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Unsaturated 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 Parent Unsaturated Fatty Acids
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 6.98 SANGSTER (1993)
Predicted Properties
Property Value Source
Water Solubility 1.510E-04 g/L ALOGPS
LogP 6.80 ALOGPS
LogP 6.59 ChemAxon
LogS -6.30 ALOGPS
pKa (strongest acidic) 4.82 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 99.95 ChemAxon
Polarizability 37.2 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Testes
  • Kidney
  • Liver
  • Epidermis
  • Thyroid Gland
  • Myelin
  • Prostate
  • Adipose Tissue
  • Lung
  • Nerve Cells
  • Platelet
  • Spleen
  • Nervous Tissues
Pathways
Name SMPDB Link KEGG Link
Alpha Linolenic Acid and Linoleic Acid Metabolism SMP00018 map00592 Link_out
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
2.94 +/- 0.058 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
14 +/- 12 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
31.6 +/- 21.7 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
31.5 +/- 25.8 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
31.7 +/- 30.4 uM Adult (>18 years old) Female Normal
Blood Detected and Quantified
5.263 +/- 2.072 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
8.50 +/- 1.58 uM Adult (>18 years old) Female Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.35 (0.03 - 0.66) uM Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
2.45 +/- 1.63 umol/mmol creatinine Adult (>18 years old) Female Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 34.3 +/- 27.8 uM Adult (>18 years old) Both Hypertension
Blood Detected and Quantified 34.0 +/- 28.6 uM Adult (>18 years old) Male Essential hypertension
Blood Detected and Quantified 34.9 +/- 26.4 uM Adult (>18 years old) Female Essential hypertension
Blood Detected and Quantified 10.27 +/- 2.11 uM Adult (>18 years old) Female Gestational diabetes mellitus (GDM)
Associated Disorders and Diseases
Disease References
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 Link_out
      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 Link_out
          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 Link_out
              Associated OMIM IDs
              DrugBank ID DB04557 Link_out
              DrugBank Metabolite ID Not Available
              Phenol Explorer Compound ID Not Available
              Phenol Explorer Metabolite ID Not Available
              FoodDB ID FDB011872
              KNApSAcK ID C00000388 Link_out
              Chemspider ID 392692 Link_out
              KEGG Compound ID C00219 Link_out
              BioCyc ID ARACHIDONIC_ACID Link_out
              BiGG ID 1586189 Link_out
              Wikipedia Link Arachidonic acid Link_out
              NuGOwiki Link HMDB01043 Link_out
              Metagene Link HMDB01043 Link_out
              METLIN ID 193 Link_out
              PubChem Compound 444899 Link_out
              PDB ID ACD Link_out
              ChEBI ID 15843 Link_out
              References
              Synthesis Reference Dai, 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. 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 Link_out
              2. 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 Link_out
              3. 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 Link_out
              4. 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 Link_out
              5. 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 Link_out
              6. 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 Link_out
              7. 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 Link_out
              8. 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 Link_out
              9. 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 Link_out
              10. 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 Link_out
              11. 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 Link_out
              12. 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 Link_out
              13. 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 Link_out
              14. 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 Link_out
              15. 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 Link_out
              16. 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 Link_out
              17. 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 Link_out
              18. 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 Link_out
              19. 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 Link_out
              20. 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 Link_out
              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 Link_out
              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 Link_out
              23. Zhao X, Imig JD: Kidney CYP450 enzymes: biological actions beyond drug metabolism. Curr Drug Metab. 2003 Feb;4(1):73-84. Pubmed: 12570747 Link_out
              24. Kudo I, Murakami M: Phospholipase A2 enzymes. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:3-58. Pubmed: 12432908 Link_out

              Enzymes

              Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 113 enzymes in total.

              Name: Fatty acid synthase
              Reactions: Not Available
              Gene Name: FASN
              Uniprot ID: P49327 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Calcium-dependent phospholipase A2
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G5
              Uniprot ID: P39877 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Group IIF secretory phospholipase A2
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G2F
              Uniprot ID: Q9BZM2 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cytosolic phospholipase A2
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G4A
              Uniprot ID: P47712 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Phospholipase A2
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G1B
              Uniprot ID: P04054 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Group XIIB secretory phospholipase A2-like protein
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G12B
              Uniprot ID: Q9BX93 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Group 10 secretory phospholipase A2
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G10
              Uniprot ID: O15496 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Galactoside-binding soluble lectin 13
              Reactions: Not Available
              Gene Name: LGALS13
              Uniprot ID: Q9UHV8 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Group IIE secretory phospholipase A2
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G2E
              Uniprot ID: Q9NZK7 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Group XIIA secretory phospholipase A2
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G12A
              Uniprot ID: Q9BZM1 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: 85/88 kDa calcium-independent phospholipase A2
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G6
              Uniprot ID: O60733 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Eosinophil lysophospholipase
              Reactions: Not Available
              Gene Name: CLC
              Uniprot ID: Q05315 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Phospholipase A2, membrane associated
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G2A
              Uniprot ID: P14555 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Group IID secretory phospholipase A2
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G2D
              Uniprot ID: Q9UNK4 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Pancreatic triacylglycerol lipase
              Reactions: Not Available
              Gene Name: PNLIP
              Uniprot ID: P16233 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Hepatic triacylglycerol lipase
              Reactions: Not Available
              Gene Name: LIPC
              Uniprot ID: P11150 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Inactive pancreatic lipase-related protein 1
              Reactions: Not Available
              Gene Name: PNLIPRP1
              Uniprot ID: P54315 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Patatin-like phospholipase domain-containing protein 3
              Reactions: Not Available
              Gene Name: PNPLA3
              Uniprot ID: Q9NST1 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Gastric triacylglycerol lipase
              Reactions: Not Available
              Gene Name: LIPF
              Uniprot ID: P07098 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Endothelial lipase
              Reactions: Not Available
              Gene Name: LIPG
              Uniprot ID: Q9Y5X9 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Bile salt-activated lipase
              Reactions: Not Available
              Gene Name: CEL
              Uniprot ID: P19835 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Pancreatic lipase-related protein 2
              Reactions: Not Available
              Gene Name: PNLIPRP2
              Uniprot ID: P54317 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Lipoprotein lipase
              Reactions: Not Available
              Gene Name: LPL
              Uniprot ID: P06858 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cytochrome P450 4A11
              Reactions:
              Arachidonic acid + Oxygen + NADPH + Hydrogen Ion unknown 20-Hydroxyeicosatetraenoic acid + NADP + Water details
              Arachidonic acid + Oxygen + NADPH + Hydrogen Ion unknown 11,12-EpETrE + NADP + Water details
              Gene Name: CYP4A11
              Uniprot ID: Q02928 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Liver carboxylesterase 1
              Reactions: Not Available
              Gene Name: CES1
              Uniprot ID: P23141 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cocaine esterase
              Reactions: Not Available
              Gene Name: CES2
              Uniprot ID: O00748 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cholinesterase
              Reactions: Not Available
              Gene Name: BCHE
              Uniprot ID: P06276 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cytosolic phospholipase A2 gamma
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G4C
              Uniprot ID: Q9UP65 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Hormone-sensitive lipase
              Reactions: Not Available
              Gene Name: LIPE
              Uniprot ID: Q05469 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Group 3 secretory phospholipase A2
              Reactions:
              Phosphatidylcholine + Water unknown 1-Acyl-sn-glycero-3-phosphocholine + Arachidonic acid details
              Gene Name: PLA2G3
              Uniprot ID: Q9NZ20 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Bile acid-CoA:amino acid N-acyltransferase
              Reactions: Not Available
              Gene Name: BAAT
              Uniprot ID: Q14032 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Acylphosphatase-2
              Reactions: Not Available
              Gene Name: ACYP2
              Uniprot ID: P14621 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Acylphosphatase-1
              Reactions: Not Available
              Gene Name: ACYP1
              Uniprot ID: P07311 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Aminoacylase-1
              Reactions: Not Available
              Gene Name: ACY1
              Uniprot ID: Q03154 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Aspartoacylase
              Reactions: Not Available
              Gene Name: ASPA
              Uniprot ID: P45381 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Aspartoacylase-2
              Reactions: Not Available
              Gene Name: ACY3
              Uniprot ID: Q96HD9 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Arachidonate 5-lipoxygenase
              Reactions:
              Arachidonic acid + Oxygen unknown leukotriene A(4) + Water details
              Arachidonic acid + Oxygen unknown 5(S)-Hydroperoxyeicosatetraenoic acid details
              Arachidonic acid + Oxygen unknown Leukotriene A4 + Water details
              Gene Name: ALOX5
              Uniprot ID: P09917 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Arachidonate 15-lipoxygenase B
              Reactions:
              Arachidonic acid + Oxygen unknown 15(S)-HPETE details
              Arachidonic acid + Oxygen unknown 8(S)-HPETE details
              Gene Name: ALOX15B
              Uniprot ID: O15296 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Arachidonate 12-lipoxygenase, 12S-type
              Reactions:
              Arachidonic acid + Oxygen unknown 12(S)-HPETE details
              Gene Name: ALOX12
              Uniprot ID: P18054 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Prostaglandin G/H synthase 2
              Reactions:
              Arachidonic acid + AH(2) + Oxygen unknown prostaglandin H(2) + A + Water details
              Arachidonic acid + Oxygen unknown Prostaglandin G2 details
              Gene Name: PTGS2
              Uniprot ID: P35354 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Prostaglandin G/H synthase 1
              Reactions:
              Arachidonic acid + AH(2) + Oxygen unknown prostaglandin H(2) + A + Water details
              Arachidonic acid + Oxygen unknown Prostaglandin G2 details
              Gene Name: PTGS1
              Uniprot ID: P23219 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Arachidonate 15-lipoxygenase
              Reactions:
              Arachidonic acid + Oxygen unknown 15(S)-HPETE details
              Gene Name: ALOX15
              Uniprot ID: P16050 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Leukotriene-B(4) omega-hydroxylase 1
              Reactions:
              Arachidonic acid + Oxygen + NADPH + Hydrogen Ion unknown 20-Hydroxyeicosatetraenoic acid + NADP + Water details
              Gene Name: CYP4F2
              Uniprot ID: P78329 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Leukotriene-B(4) omega-hydroxylase 2
              Reactions:
              Arachidonic acid + Oxygen + NADPH + Hydrogen Ion unknown 20-Hydroxyeicosatetraenoic acid + NADP + Water details
              Gene Name: CYP4F3
              Uniprot ID: Q08477 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cytochrome P450 3A4
              Reactions: Not Available
              Gene Name: CYP3A4
              Uniprot ID: P08684 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cytochrome P450 2C9
              Reactions: Not Available
              Gene Name: CYP2C9
              Uniprot ID: P11712 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cytochrome P450 2C19
              Reactions: Not Available
              Gene Name: CYP2C19
              Uniprot ID: P33261 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Cytosolic acyl coenzyme A thioester hydrolase
              Reactions:
              Arachidonyl-CoA + Water unknown Coenzyme A + Arachidonic acid details
              Gene Name: ACOT7
              Uniprot ID: O00154 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Acyl-coenzyme A thioesterase 2, mitochondrial
              Reactions:
              Arachidonyl-CoA + Water unknown Coenzyme A + Arachidonic acid details
              Gene Name: ACOT2
              Uniprot ID: P49753 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Acyl-coenzyme A thioesterase 4
              Reactions:
              Arachidonyl-CoA + Water unknown Coenzyme A + Arachidonic acid details
              Gene Name: ACOT4
              Uniprot ID: Q8N9L9 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Transporters
              Name: Long-chain fatty acid transport protein 1
              Reactions: Not Available
              Gene Name: SLC27A1
              Uniprot ID: Q6PCB7 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Solute carrier organic anion transporter family member 2A1
              Reactions: Not Available
              Gene Name: SLCO2A1
              Uniprot ID: Q92959 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA