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 14:17:50 UTC |
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Update Date | 2022-03-07 02:49:15 UTC |
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HMDB ID | HMDB0002368 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Nervonic acid |
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Description | Nervonic acid is a long chain unsaturated fatty acid that is enriched in sphingomyelin. It consists of choline, sphingosine, phosphoric acid, and fatty acid. Nervonic acid may enhance the brain functions and prevent demyelination (Chemical Land21). Research shows that there is negative relationship between nervonic acid and obesity-related risk factors (PMID:16394593 ). Demyelination in adrenoleukodystrophy (ALD) is associated with an accumulation of very long chain saturated fatty acids stemming from a genetic defect in the peroxisomal beta oxidation system responsible for the chain shortening of these fatty acids. Sphingolipids from post mortem ALD brain have decreased levels of nervonic acid, 24:1(n-9), and increased levels of stearic acid, 18:0. (PMID:8072429 ). |
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Structure | CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O InChI=1S/C24H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9- |
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Synonyms | Value | Source |
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(Z)-15-Tetracosenoic acid | ChEBI | (Z)-Tetracos-15-enoic acid | ChEBI | 15cis-Tetracosenoic acid | ChEBI | cis-15-Tetracosenoic acid | ChEBI | cis-Delta(15)-Tetracosenoic acid | ChEBI | Nervonsaeure | ChEBI | Selacholeic acid | ChEBI | (Z)-15-Tetracosenoate | Generator | (Z)-Tetracos-15-enoate | Generator | 15cis-Tetracosenoate | Generator | cis-15-Tetracosenoate | Generator | cis-delta(15)-Tetracosenoate | Generator | cis-Δ(15)-tetracosenoate | Generator | cis-Δ(15)-tetracosenoic acid | Generator | Selacholeate | Generator | Nervonate | Generator | (15Z)-Tetracos-15-enoate | HMDB | (15Z)-Tetracos-15-enoic acid | HMDB | (15Z)-Tetracosenoate | HMDB | (15Z)-Tetracosenoic acid | HMDB | 15-Tetracosenoate | HMDB | 15-Tetracosenoic acid | HMDB | 15Z-Tetracosenoate | HMDB | 15Z-Tetracosenoic acid | HMDB | cis-15-Teracosenoate | HMDB | cis-15-Teracosenoic acid | HMDB | cis-15-Tetracosenate | HMDB | cis-15-Tetracosenic acid | HMDB | cis-Selacholeate | HMDB | cis-Selacholeic acid | HMDB | trans-Tetracos-15-enoic acid | HMDB | (15Z)-15-Tetracosenoic acid | HMDB | FA(24:1(15Z)) | HMDB | FA(24:1n9) | HMDB | Nevonic acid | HMDB | Nervonic acid | ChEBI |
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Chemical Formula | C24H46O2 |
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Average Molecular Weight | 366.6208 |
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Monoisotopic Molecular Weight | 366.349780716 |
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IUPAC Name | (15Z)-tetracos-15-enoic acid |
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Traditional Name | nervonic acid |
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CAS Registry Number | 506-37-6 |
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SMILES | CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C24H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9- |
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InChI Key | GWHCXVQVJPWHRF-KTKRTIGZSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 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 | Very long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Very 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 | |
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Physical Properties |
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State | Liquid |
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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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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Spectra |
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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 - Nervonic acid GC-MS (1 TMS) | splash10-00nb-5900000000-969f119cba8683e5cc50 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Nervonic acid GC-MS (Non-derivatized) | splash10-00nb-5900000000-969f119cba8683e5cc50 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nervonic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f6x-9782000000-97d131b02e4a98acfe12 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nervonic acid GC-MS (1 TMS) - 70eV, Positive | splash10-00dr-9551000000-d11282fde9bc72e71510 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nervonic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nervonic 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 - Nervonic acid Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-014i-0009000000-77254b7f9e0c5adec2c5 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nervonic acid Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-05ur-9300000000-c24f47c8ec64393d34b0 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nervonic acid Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-0api-9000000000-f9dc5919bdde58922d07 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nervonic acid 35V, Negative-QTOF | splash10-014i-0009000000-b5ce223be566232389ce | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 10V, Positive-QTOF | splash10-0002-0009000000-23437c970e4496314dc2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 20V, Positive-QTOF | splash10-0601-4529000000-0a095c0f2e7f69a7046c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 40V, Positive-QTOF | splash10-0a4l-9873000000-0479aea7f81e735a49b4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 10V, Negative-QTOF | splash10-014i-0009000000-6bdffa41d37f32273117 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 20V, Negative-QTOF | splash10-01ba-0009000000-f28d20de75190fe2dfd6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 40V, Negative-QTOF | splash10-0a4l-9113000000-2bdab238903303f33f49 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 10V, Negative-QTOF | splash10-014i-0009000000-340806f152b23d48ad56 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 20V, Negative-QTOF | splash10-014j-1009000000-ecb8e3e7292d693c5e2d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 40V, Negative-QTOF | splash10-0006-9011000000-3a65628878739cc356f3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 10V, Positive-QTOF | splash10-014j-2009000000-966c9a99f927842d86e9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 20V, Positive-QTOF | splash10-00l2-8349000000-44259b5853a420e306d6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nervonic acid 40V, Positive-QTOF | splash10-0aou-9100000000-3338b5c4d18e533bf611 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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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 | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 34.532 +/- 23.730 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 0.070 +/- 0.006 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.900 +/- 0.974 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 68.5 +/- 18.2 uM | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 77.5 +/- 21.6 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 | 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 ]
- 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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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 | FDB002934 |
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KNApSAcK ID | C00001230 |
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Chemspider ID | 4444565 |
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KEGG Compound ID | C08323 |
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BioCyc ID | Not Available |
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BiGG ID | 2218012 |
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Wikipedia Link | Nervonic acid |
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METLIN ID | 262 |
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PubChem Compound | 5281120 |
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PDB ID | Not Available |
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ChEBI ID | 44247 |
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Food Biomarker Ontology | Not Available |
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VMH ID | NRVNC |
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MarkerDB ID | MDB00000392 |
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Good Scents ID | rw1268611 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Bitsanis D, Crawford MA, Moodley T, Holmsen H, Ghebremeskel K, Djahanbakhch O: Arachidonic acid predominates in the membrane phosphoglycerides of the early and term human placenta. J Nutr. 2005 Nov;135(11):2566-71. [PubMed:16251612 ]
- Laasonen M, Erkkila AT, Isotalo E, Maenpaa PK, Pulkkinen JJ, Virsu V, Haapanen ML: Serum lipid fatty acids and temporal processing acuity in children with oral clefts. Prostaglandins Leukot Essent Fatty Acids. 2006 Apr;74(4):263-70. Epub 2006 Mar 20. [PubMed:16545557 ]
- Karlsson M, Marild S, Brandberg J, Lonn L, Friberg P, Strandvik B: Serum phospholipid fatty acids, adipose tissue, and metabolic markers in obese adolescents. Obesity (Silver Spring). 2006 Nov;14(11):1931-9. [PubMed:17135608 ]
- Oda E, Hatada K, Kimura J, Aizawa Y, Thanikachalam PV, Watanabe K: Relationships between serum unsaturated fatty acids and coronary risk factors: negative relations between nervonic acid and obesity-related risk factors. Int Heart J. 2005 Nov;46(6):975-85. [PubMed:16394593 ]
- Sargent JR, Coupland K, Wilson R: Nervonic acid and demyelinating disease. Med Hypotheses. 1994 Apr;42(4):237-42. [PubMed:8072429 ]
- 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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