Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 15:12:20 UTC |
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Update Date | 2022-03-07 02:49:17 UTC |
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HMDB ID | HMDB0002925 |
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Secondary Accession Numbers | - HMDB0006735
- HMDB02925
- HMDB06735
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Metabolite Identification |
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Common Name | Dihomo-gamma-linolenic acid |
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Description | 8,11,14-Eicosatrienoic acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 8,11,14-Eicosatrienoic acid is also known as Dihomo-gamma-linolenic acid (DGLA). In physiological literature, it is given the name 20:3(n-6). DGLA is the elongation product of the 18 carbon gamma-linolenic acid (GLA). DGLA can be converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect. DGLA competes with arachadonic acid for COX and lipoxygenase, inhibiting the production of arachadonic acid's eicosanoids. |
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Structure | |
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Synonyms | Not Available |
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Chemical Formula | C20H34O2 |
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Average Molecular Weight | 306.4828 |
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Monoisotopic Molecular Weight | 306.255880332 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 1783-84-2 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12- |
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InChI Key | HOBAELRKJCKHQD-QNEBEIHSSA-N |
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Chemical Taxonomy |
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Classification | Not classified |
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Ontology |
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Physiological effect | Not Available |
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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 | Not Available | Not Available |
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Experimental Chromatographic Properties |
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Predicted Molecular Properties | Not Available |
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Predicted Chromatographic Properties | Predicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Dihomo-gamma-linolenic acid,1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C | 2391.4 | Semi standard non polar | 33892256 | Dihomo-gamma-linolenic acid,1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C | 2367.2 | Standard non polar | 33892256 | Dihomo-gamma-linolenic acid,1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C | 2591.8 | Standard polar | 33892256 | Dihomo-gamma-linolenic acid,1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C | 2638.4 | Semi standard non polar | 33892256 | Dihomo-gamma-linolenic acid,1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C | 2564.4 | Standard non polar | 33892256 | Dihomo-gamma-linolenic acid,1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C | 2626.9 | Standard polar | 33892256 |
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Spectra |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | - Adipose Tissue
- Epidermis
- Placenta
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.542 +/- 0.005 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 3.61 +/- 2.1 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 118.408 +/- 39.774 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 0.420 +/- 0.207 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.54 +/- 0.005 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 84.8 +/- 30.8 uM | Adult (>18 years old) | Not Specified | Isovaleric acidemia | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Not Specified | Premature neonates | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Attachment loss | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Periodontal Probing Depth | | details |
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Associated Disorders and Diseases |
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Disease References | 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 ]
| 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 ]
- 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 ]
| Attachment loss |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Periodontal Probing Depth |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
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Associated OMIM IDs | |
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External Links |
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External Links | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Abraham RD, Riemersma RA, Elton RA, Macintyre C, Oliver MF: Effects of safflower oil and evening primrose oil in men with a low dihomo-gamma-linolenic level. Atherosclerosis. 1990 Apr;81(3):199-208. [PubMed:2112389 ]
- Du L, Yermalitsky V, Hachey DL, Jagadeesh SG, Falck JR, Keeney DS: A biosynthetic pathway generating 12-hydroxy-5,8,14-eicosatrienoic acid from arachidonic acid is active in mouse skin microsomes. J Pharmacol Exp Ther. 2006 Jan;316(1):371-9. Epub 2005 Sep 16. [PubMed:16169934 ]
- Hamilton RM, Gillespie CT, Cook HW: Relationships between levels of essential fatty acids and zinc in plasma of cystic fibrosis patients. Lipids. 1981 May;16(5):374-6. [PubMed:6789026 ]
- Thijs C, Houwelingen A, Poorterman I, Mordant A, van den Brandt P: Essential fatty acids in breast milk of atopic mothers: comparison with non-atopic mothers, and effect of borage oil supplementation. Eur J Clin Nutr. 2000 Mar;54(3):234-8. [PubMed:10713746 ]
- Emken EA, Adlof RO, Duval SM, Nelson GJ: Influence of dietary arachidonic acid on metabolism in vivo of 8cis,11cis,14-eicosatrienoic acid in humans. Lipids. 1997 Apr;32(4):441-8. [PubMed:9113634 ]
- Melnik BC, Plewig G: Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1? J Am Acad Dermatol. 1989 Sep;21(3 Pt 1):557-63. [PubMed:2550526 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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