Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-10-23 11:28:21 UTC |
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Update Date | 2022-03-07 02:49:25 UTC |
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HMDB ID | HMDB0005060 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Eicosadienoic acid |
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Description | Eicosadienoic acid is an omega-6 fatty acid found in human milk (PMID: 15256803 ). Omega-6 fatty acids are a family of unsaturated fatty acids which have in common a carbon-carbon double bond in the n−6 position; that is, the sixth bond from the end of the fatty acid. The biological effects of the omega−6 fatty acids are largely mediated by their conversion to n-6 eicosanoids that bind to diverse receptors found in every tissue of the body. Eicosadienoic acid has been identified in the human placenta (PMID: 32033212 ). |
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Structure | CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9- |
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Synonyms | Value | Source |
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(11Z,14Z)-Eicosa-11,14-dienoic acid | ChEBI | (11Z,14Z)-Eicosadienoic acid | ChEBI | (11Z,14Z)-Icosa-11,14-dienoic acid | ChEBI | 11,14-Eicosadienoic acid | ChEBI | 11,14-Icosadienoic acid | ChEBI | (11Z,14Z)-Eicosa-11,14-dienoate | Generator | (11Z,14Z)-Eicosadienoate | Generator | (11Z,14Z)-Icosa-11,14-dienoate | Generator | 11,14-Eicosadienoate | Generator | 11,14-Icosadienoate | Generator | Eicosadienoate | Generator | 11, 14-Icosadienoate | HMDB | 11, 14-Icosadienoic acid | HMDB | 11,14-trans-Eicosadienoic acid | HMDB | delta11,14-20:2 | HMDB | Eicosa-11,14-dienoic acid | HMDB | Eicosa-11,14-dienoic acid, (Z,Z)-isomer | HMDB | N-6 Eicosadienoic acid | HMDB | Dihomolinoleate | HMDB | (11Z,14Z)-Icosadienoate | HMDB | (11Z,14Z)-11,14-Eicosadienate | HMDB | (11Z,14Z)-11,14-Eicosadienic acid | HMDB | (11Z,14Z)-11,14-Eicosadienoate | HMDB | (11Z,14Z)-11,14-Eicosadienoic acid | HMDB | 11,14-all-cis-Eicosadienoate | HMDB | 11,14-all-cis-Eicosadienoic acid | HMDB | 11-cis,14-cis-Eicosadienoate | HMDB | 11-cis,14-cis-Eicosadienoic acid | HMDB | Bishomolinoleate | HMDB | Bishomolinoleic acid | HMDB | Dihomo-linoleate (20:2n6) | HMDB | Dihomo-linoleic acid (20:2n6) | HMDB | FA(20:2(11Z,14Z)) | HMDB | Homo-gamma-linoleate | HMDB | Homo-gamma-linoleic acid | HMDB | Homo-γ-linoleate | HMDB | Homo-γ-linoleic acid | HMDB | all-cis-11,14-Eicosadienoate | HMDB | all-cis-11,14-Eicosadienoic acid | HMDB | cis,cis-Eicosa-11,14-dienoate | HMDB | cis,cis-Eicosa-11,14-dienoic acid | HMDB | cis,cis-delta11,14-Eicosadienoate | HMDB | cis,cis-delta11,14-Eicosadienoic acid | HMDB | cis,cis-Δ11,14-eicosadienoate | HMDB | cis,cis-Δ11,14-eicosadienoic acid | HMDB | cis-11,cis-14-Eicosadienoate | HMDB | cis-11,cis-14-Eicosadienoic acid | HMDB | delta11,14-Eicosadienoate | HMDB | delta11,14-Eicosadienoic acid | HMDB | Δ11,14-eicosadienoate | HMDB | Δ11,14-eicosadienoic acid | HMDB | FA(20:2n6) | HMDB | Eicosadienoic acid | ChEBI |
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Chemical Formula | C20H36O2 |
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Average Molecular Weight | 308.4986 |
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Monoisotopic Molecular Weight | 308.271530396 |
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IUPAC Name | (11Z,14Z)-icosa-11,14-dienoic acid |
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Traditional Name | eicosadienoic acid |
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CAS Registry Number | 5598-38-9 |
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SMILES | CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9- |
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InChI Key | XSXIVVZCUAHUJO-HZJYTTRNSA-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 | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Eicosadienoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9760000000-cd3039251f27ed659833 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Eicosadienoic acid GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9652000000-051c308924d68202698f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Eicosadienoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Eicosadienoic 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 - Eicosadienoic acid LC-ESI-IT , negative-QTOF | splash10-000i-0091000000-cd5567f72a97a19a5daa | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid n/a 21V, positive-QTOF | splash10-0006-0290000000-26edae55398bbe6d8f14 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 30V, positive-QTOF | splash10-003v-9200000000-f117dd4d613f97c9e9a1 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 33V, positive-QTOF | splash10-003u-9100000000-64feb0d0359edf0e55fa | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 37V, positive-QTOF | splash10-003u-9100000000-1c5be01a286361015756 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 40V, positive-QTOF | splash10-005c-9100000000-2af5db21026406ee4f51 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 44V, positive-QTOF | splash10-005c-9100000000-900bb2bb1942a2772e06 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid n/a 21V, positive-QTOF | splash10-05o0-1900000000-87b112cb6d02616a7390 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 0V, positive-QTOF | splash10-0a4i-0009000000-66380db5e2f48c28d914 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 1V, positive-QTOF | splash10-0a4i-0009000000-37933ac7549ff468e6e0 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 3V, positive-QTOF | splash10-0a4i-0019000000-139b1c14ace122806206 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 4V, positive-QTOF | splash10-0a4i-0049000000-bea23a8f63f68b2a2579 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 7V, positive-QTOF | splash10-052g-3594000000-9f6dd586ee4aa178e78e | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid n/a 21V, positive-QTOF | splash10-0hka-0930000000-500174f550638fdb0b03 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid n/a 21V, positive-QTOF | splash10-00di-0490000000-80d1e0e8b9b35e163450 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 4V, positive-QTOF | splash10-0006-0090000000-cf7b1131f470250aedcb | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 6V, positive-QTOF | splash10-0006-0090000000-32033519d24a370bbb6e | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 10V, positive-QTOF | splash10-0006-2590000000-f57018cf6f280ddd27bd | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 14V, positive-QTOF | splash10-059w-7930000000-7f2165e3d0add956aa59 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 17V, positive-QTOF | splash10-053s-9600000000-4f5ff0e39e1f3cb65e88 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 22V, positive-QTOF | splash10-053s-9300000000-8f9cd251a7bb707f1544 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid Orbitrap 28V, positive-QTOF | splash10-001m-9100000000-176d923c10fc2cf41b6c | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid n/a 21V, positive-QTOF | splash10-00di-1890000000-ea581730d6da2112857d | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid n/a 21V, positive-QTOF | splash10-014i-9000000000-1170a17e0bd60829ce3f | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eicosadienoic acid n/a 21V, positive-QTOF | splash10-001i-9000000000-3e1931835afb9d465af4 | 2020-07-22 | HMDB team, MONA | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.418 +/- 0.162 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 20.3 +/- 6.8 uM | Adult (>18 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 15.0730 +/- 4.182 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 0.352 +/- 0.029 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 16.9 +/- 4.8 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 |
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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 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB012619 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4944228 |
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KEGG Compound ID | C16525 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 6439848 |
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PDB ID | Not Available |
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ChEBI ID | 73731 |
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Food Biomarker Ontology | Not Available |
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VMH ID | EIDI1114AC |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1210811 |
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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 | - Minda H, Kovacs A, Funke S, Szasz M, Burus I, Molnar S, Marosvolgyi T, Decsi T: Changes of fatty acid composition of human milk during the first month of lactation: a day-to-day approach in the first week. Ann Nutr Metab. 2004;48(3):202-9. Epub 2004 Jul 13. [PubMed:15256803 ]
- 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 ]
- Lipid Maps (LMFA01030130) [Link]
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