Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:08 UTC |
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HMDB ID | HMDB0001043 |
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Secondary Accession Numbers | - HMDB0060102
- HMDB01043
- HMDB60102
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Metabolite Identification |
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Common Name | Arachidonic acid |
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Description | 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. 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 ). The beneficial effects of omega-3 fatty acids are believed to be due in part to selective alteration of arachidonate metabolism that involves cyclooxygenase (COX) enzymes (PMID: 23371504 ). 9-Oxononanoic acid (9-ONA), one of the major products of peroxidized fatty acids, was found to stimulate the activity of phospholipase A2 (PLA2), the key enzyme to initiate the arachidonate cascade and eicosanoid production (PMID: 23704812 ). Arachidonate lipoxygenase (ALOX) enzymes metabolize arachidonic acid to generate potent inflammatory mediators and play an important role in inflammation-associated diseases (PMID: 23404351 ). |
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Structure | CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O 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- |
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Synonyms | Value | Source |
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(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid | ChEBI | (5Z,8Z,11Z,14Z)-Icosatetraenoic acid | ChEBI | AA | ChEBI | all-cis-5,8,11,14-Eicosatetraenoic acid | ChEBI | ARA | ChEBI | Arachidonate | ChEBI | Arachidonsaeure | ChEBI | cis-5,8,11,14-Eicosatetraenoic acid | ChEBI | cis-Delta(5,8,11,14)-Eicosatetraenoic acid | ChEBI | 5Z,8Z,11Z,14Z-Eicosatetraenoic acid | Kegg | (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid | Kegg | (5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoate | Generator | (5Z,8Z,11Z,14Z)-Icosatetraenoate | Generator | all-cis-5,8,11,14-Eicosatetraenoate | Generator | cis-5,8,11,14-Eicosatetraenoate | Generator | cis-delta(5,8,11,14)-Eicosatetraenoate | Generator | cis-Δ(5,8,11,14)-eicosatetraenoate | Generator | cis-Δ(5,8,11,14)-eicosatetraenoic acid | Generator | 5Z,8Z,11Z,14Z-Eicosatetraenoate | Generator | (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoate | Generator | (all-Z)-5,8,11,14-Eicosatetraenoate | HMDB | (all-Z)-5,8,11,14-Eicosatetraenoic acid | HMDB | 5,8,11,14-all-cis-Eicosatetraenoate | HMDB | 5,8,11,14-all-cis-Eicosatetraenoic acid | HMDB | 5,8,11,14-Eicosatetraenoate | HMDB | 5,8,11,14-Eicosatetraenoic acid | HMDB | 5-cis,8-cis,11-cis,14-cis-Eicosatetraenoate | HMDB | 5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acid | HMDB | cis-D5,8,11,14-Eicosatetraenoate | HMDB | cis-D5,8,11,14-Eicosatetraenoic acid | HMDB | Immunocytophyte | HMDB | Arachidonate, sodium | HMDB | Arachidonic acid, (all-Z)-isomer, 3H-labeled | HMDB | Arachidonic acid, ammonium salt, (all-Z)-isomer | HMDB | Arachidonic acid, cerium salt, (all-Z)-isomer | HMDB | Arachidonic acid, sodium salt | HMDB | Arachidonic acid, sodium salt, (all-Z)-isomer | HMDB | Vitamin F | HMDB | Arachidonic acid, cesium salt, (all-Z)-isomer | HMDB | Arachidonic acid, lithium salt, (all-Z)-isomer | HMDB | Arachidonic acid, potassium salt, (all-Z)-isomer | HMDB | Sodium arachidonate | HMDB | Arachidonic acid, (all-Z)-isomer, 1-(14)C-labeled | HMDB | Arachidonic acid, zinc salt, (all-Z)-isomer | HMDB | FA(20:4(5Z,8Z,11Z,14Z)) | HMDB | FA(20:4n6) | HMDB |
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Chemical Formula | C20H32O2 |
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Average Molecular Weight | 304.4669 |
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Monoisotopic Molecular Weight | 304.240230268 |
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IUPAC Name | (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid |
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Traditional Name | arachidonic acid |
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CAS Registry Number | 506-32-1 |
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SMILES | CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O |
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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- |
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InChI Key | YZXBAPSDXZZRGB-DOFZRALJSA-N |
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Chemical Taxonomy |
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Description | 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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Long-chain fatty acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | 6.98 | SANGSTER (1993) |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Arachidonic acid GC-MS (1 TMS) | splash10-005c-9800000000-87c290971fc8a628fb23 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Arachidonic acid GC-MS (Non-derivatized) | splash10-005c-9800000000-87c290971fc8a628fb23 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Arachidonic acid GC-EI-TOF (Non-derivatized) | splash10-0006-6900000000-6870df266b6c73f2a4a1 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Arachidonic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-7390000000-7004b9cd28a9b3d9c991 | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Arachidonic acid GC-MS (1 TMS) - 70eV, Positive | splash10-05i9-9252000000-475d13959ee8ce889646 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Arachidonic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Arachidonic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF | splash10-0nmi-0913000000-95846e8d5e8afd29664b | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 10V, Negative-QTOF | splash10-005l-0902100000-6fc8730bd28daa779b66 | 2017-08-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 20V, Negative-QTOF | splash10-005l-0902100000-6fc8730bd28daa779b66 | 2017-08-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid ESI-TOF , Negative-QTOF | splash10-005l-0902100000-6fc8730bd28daa779b66 | 2017-08-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 10V, Negative-QTOF | splash10-0udi-0009000000-4dd23c77f8e48c0ab9ec | 2017-08-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 30V, Negative-QTOF | splash10-0udi-0009000000-4dd23c77f8e48c0ab9ec | 2017-08-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 10V, Negative-QTOF | splash10-0udi-0009000000-6bd9d0477c122d3eed94 | 2017-09-12 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 20V, Negative-QTOF | splash10-0udi-0009000000-510ea33e558fa238a1d2 | 2017-09-12 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid ESI-TOF , Negative-QTOF | splash10-0udi-0009000000-73a6b21464acba15463c | 2017-09-12 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 10V, Negative-QTOF | splash10-0udi-0009000000-4dd23c77f8e48c0ab9ec | 2017-09-12 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid ESI-TOF 30V, Negative-QTOF | splash10-0udi-0049000000-102d050109d3c78b1a25 | 2017-09-12 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid LC-ESI-IT , negative-QTOF | splash10-0a4i-0090000000-2fb9003e782ec3d05e20 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid LC-ESI-QTOF , negative-QTOF | splash10-0nmi-0913000000-95846e8d5e8afd29664b | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid LC-ESI-TOF , negative-QTOF | splash10-0udi-0009000000-6bd9d0477c122d3eed94 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid LC-ESI-TOF , negative-QTOF | splash10-0udi-0009000000-510ea33e558fa238a1d2 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid LC-ESI-TOF , negative-QTOF | splash10-0udi-0049000000-102d050109d3c78b1a25 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid 10V, Positive-QTOF | splash10-0udi-0009000000-6bd9d0477c122d3eed94 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid 20V, Positive-QTOF | splash10-0udi-0009000000-510ea33e558fa238a1d2 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Arachidonic acid 6V, Positive-QTOF | splash10-0a4i-1934000000-3fb5938d1b4795217a97 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arachidonic acid 10V, Positive-QTOF | splash10-0a4r-1196000000-a42ea66033eb9771d36d | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arachidonic acid 20V, Positive-QTOF | splash10-0a4j-5691000000-2bc7b1ae5487233dfce8 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arachidonic acid 40V, Positive-QTOF | splash10-0007-7950000000-b15a8d382a4b3ad62d08 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arachidonic acid 10V, Negative-QTOF | splash10-0udi-0029000000-28a9bbfed5fabd10c0c2 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arachidonic acid 20V, Negative-QTOF | splash10-0zfr-2079000000-3f6e64ef7522a793e9a9 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arachidonic acid 40V, Negative-QTOF | splash10-0a4i-9130000000-9c0c8bb5fc8e30bf53c7 | 2017-07-26 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-22 | Wishart Lab | View Spectrum |
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Disease References | Gestational diabetes |
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- 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 |
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- 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 ]
| Essential hypertension |
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- 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 |
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- 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 ]
| Isovaleric acidemia |
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- 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 ]
| Bladder infections |
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- 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 |
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- 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 ]
- 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 ]
- 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 ]
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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