Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:36:51 UTC |
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Update Date | 2020-06-04 22:55:30 UTC |
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BMDB ID | BMDB0000806 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Myristic acid |
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Description | Myristic acid, also known as 14 or tetradecanoate, 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. Myristic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Myristic acid exists in all living species, ranging from bacteria to humans. Myristic acid participates in a number of enzymatic reactions, within cattle. In particular, Myristic acid can be biosynthesized from trans-tetra-dec-2-enoic acid through the action of the enzyme fatty acid synthase. enoyl reductase domain. In addition, Myristic acid and malonic acid can be converted into 3-oxohexadecanoic acid through the action of the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In cattle, myristic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Myristic acid is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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1-Tetradecanecarboxylic acid | ChEBI | 14 | ChEBI | 14:0 | ChEBI | 14:00 | ChEBI | Acide tetradecanoique | ChEBI | C14 | ChEBI | CH3-[CH2]12-COOH | ChEBI | Myristinsaeure | ChEBI | N-Tetradecan-1-Oic acid | ChEBI | N-Tetradecanoic acid | ChEBI | N-Tetradecoic acid | ChEBI | Tetradecoic acid | ChEBI | Tetradecanoate | Kegg | 1-Tetradecanecarboxylate | Generator | N-Tetradecan-1-Oate | Generator | N-Tetradecanoate | Generator | N-Tetradecoate | Generator | Tetradecoate | Generator | Tetradecanoic acid | Generator | Myristate | Generator | 1-Tridecanecarboxylate | HMDB | 1-Tridecanecarboxylic acid | HMDB | Crodacid | HMDB | Myristic acid pure | HMDB | Myristoate | HMDB | Myristoic acid | HMDB | Tetradecanoic (myristic) acid | HMDB | Acid, tetradecanoic | HMDB | Acid, myristic | HMDB | FA(14:0) | HMDB |
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Chemical Formula | C14H28O2 |
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Average Molecular Weight | 228.3709 |
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Monoisotopic Molecular Weight | 228.20893014 |
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IUPAC Name | tetradecanoic acid |
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Traditional Name | myristic acid |
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CAS Registry Number | 544-63-8 |
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SMILES | CCCCCCCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16) |
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InChI Key | TUNFSRHWOTWDNC-UHFFFAOYSA-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
- 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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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 53.9 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.00107 mg/mL | Not Available | LogP | 6.11 | SANGSTER (1993) |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-017i-2910000000-66b35fb8449ba9de9cd6 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-017i-2910000000-66b35fb8449ba9de9cd6 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-0910000000-f45703c464ca75f98f26 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9700000000-ec8d81e37bc3b8531c99 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0079-9330000000-5ec01705dfacc992be28 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-004i-0090000000-73ac1cfb8731e6318cc5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-004i-1090000000-3aa768974da0ea81c1c9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0090000000-22cd107a87b9acf058c5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0090000000-2f7bb32e4b42206d851d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-2090000000-d45cffc15e2efbd45cd6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-001i-9200000000-dbca68238dfebab35251 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004r-9000000000-26827be8f8c2a4fbfd75 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-0006-0090000000-110165b889d231d09d59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0006-0090000000-110165b889d231d09d59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0006-0090000000-110165b889d231d09d59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0006-0090000000-110165b889d231d09d59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-004i-0090000000-91f4f874b25705464fb0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0090000000-15225a799e0a0bcff7c7 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0290000000-b88426a2003ceec57e30 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-5940000000-6c73dc0032502abe4fc4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9300000000-bde9bfcd2889066fc853 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0290000000-b88426a2003ceec57e30 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-5940000000-6c73dc0032502abe4fc4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9300000000-bde9bfcd2889066fc853 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0190000000-a32f141c7b5af0bc4de1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-1490000000-14bfb0d0344d7cf63443 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9400000000-512abb1322963024336f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0190000000-a32f141c7b5af0bc4de1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-1490000000-14bfb0d0344d7cf63443 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9400000000-512abb1322963024336f | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-06xx-9200000000-4fdd41f0461ff5186901 | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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Biospecimen Locations | - Adipose Tissue
- Blood
- Epidermis
- Liver
- Mammary Gland
- Milk
- Oocyte
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Spleen
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Pathways | |
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Normal Concentrations |
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Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 5136.47 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 4775.21 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 104050.78 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 132744.23 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 115186.7 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 120872.0989 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 151726.86 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 140692.18 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 147041.5 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected and Quantified | 138051.74 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1926.69 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1445.0177 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 16814.752 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 16157.93 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 15107.00 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10.5 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 14.4 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 17.5 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 35.64 +/- 6.48 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 41.48 +/- 6.48 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 17.52 +/- 1.14 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 7.14 +/- 0.65 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 30.39 +/- 0.20 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 17953.243 +/- 5254.608 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 39.585 +/- 0.59 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 84.5 +/- 26.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 53.5 +/- 15.7 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19660.990 +/- 4291.263 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19004.164 +/- 3809.591 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6874.78 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6568.26 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1445.0177 uM | Not Specified | Not Specified | Normal | | details | Oocyte | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 3.3 +/- 0.6 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 3.3 +/- 0.6 uM | Not Specified | Not Specified | Normal | | details | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details |
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External Links |
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HMDB ID | HMDB0000806 |
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DrugBank ID | DB08231 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB031009 |
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KNApSAcK ID | C00001228 |
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Chemspider ID | 10539 |
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KEGG Compound ID | C06424 |
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BioCyc ID | CPD-7836 |
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BiGG ID | 215851 |
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Wikipedia Link | Myristic_acid |
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METLIN ID | 196 |
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PubChem Compound | 11005 |
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PDB ID | Not Available |
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ChEBI ID | 28875 |
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References |
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Synthesis Reference | Greaves, W. S.; Linstead, R. P.; Shephard, B. R.; Thomas, S. L. S.; Weedon, B. C. L. Anodic syntheses. I. New syntheses of stearic, myristic, and other acids. Journal of the Chemical Society (1950), 3326-30. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
- Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
- GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
- van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
- Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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