arachidonic acid

view
  • Name: arachidonic acid
  • Description: Arachidonic acid is an unsaturated, 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 i... s formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic 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 which 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 ). (MeSH:D016718, HMDB0001043)
Overview of age-variations
Age group comparisons
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
18384253 Age 24.5 ± 3, Gender ⚥ 0.92 (mean value of the compound area) LC-MS; GC-MS plasma
18384253 Age 40.8 ± 5.6, Gender ⚥ 0.97 (mean value of the compound area) LC-MS; GC-MS plasma
18384253 Age 55.6 ± 3.7, Gender ⚥ 1.02 (mean value of the compound area) LC-MS; GC-MS plasma
Linear regression
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
log2 ratio/log2(FC)
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
Summary
  • Synonym:
    ARA
  • Chemical Formula:
    C20H32O2
  • Exact Mass g/mol:
    304.2402000
  • Systematic name:
    cis-5,8,11,14-eicosatetraenoic acid;(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid; all-cis-5,8,11,14-eicosatetraenoic acid
  • SMILES:
    CCCCCC=CCC=CCC=CCC=CCCCC(=O)O
  • InChI:
    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
  • CAS number:
    93444-49-6; 506-32-1
Related resources
Pathway info P = product of S = substrate of
Metabolite sources and localization
  • Metabolite location:
    Human organism, Body part, Human body biofluids, Biofluid tissues, Blood, Blood cells, Platelet, Plasma, Cerebrospinal fluid, Saliva, Urine, Organ, Gland, Gonad, Testicle, Thyroid gland, Intestine, Kidney, Liver, Lung, Muscle, Skeletal muscle, Pancreas, Placenta, Prostate, Skin, Skin tissue, Epidermis, Spleen, Tissue, Adipose tissue, Connective tissue, Connective tissue cell, Fibroblast, Nervous tissue, Nervous tissue cells, Nerve cell, Neuron, Subcellular level of nervous cells, Myelin sheath, Excreta material, Feces
  • Metabolite source:
    Homo sapiens, endogenous metabolite
Age-variations
Age group comparisons
Method: LC-MS; GC-MS
Sample: plasma
PubMed PMID: 18384253
Search the database by metabolite name or synonym