Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:19:09 UTC |
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Update Date | 2020-06-04 21:20:41 UTC |
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BMDB ID | BMDB0000062 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | L-Carnitine |
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Description | L-Carnitine, also known as carnitine d-form, belongs to the class of organic compounds known as carnitines. These are organic compounds containing the quaternary ammonium compound carnitine. L-Carnitine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). L-Carnitine participates in a number of enzymatic reactions, within cattle. In particular, Propionyl-CoA and L-carnitine can be converted into propionylcarnitine through its interaction with the enzyme carnitine O-acetyltransferase. In addition, Acetyl-CoA and L-carnitine can be converted into L-acetylcarnitine through its interaction with the enzyme carnitine O-acetyltransferase. In cattle, L-carnitine is involved in the metabolic pathway called the oxidation OF branched-chain fatty acids pathway. |
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Structure | |
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Synonyms | Value | Source |
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(-)-Carnitine | ChEBI | (-)-L-Carnitine | ChEBI | 3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium hydroxide, inner salt | ChEBI | Carnicor | ChEBI | Carnitene | ChEBI | Carnitine | ChEBI | Carnitor | ChEBI | Karnitin | ChEBI | Levocarnitine | ChEBI | Vitamin BT | ChEBI | L-gamma-Trimethyl-beta-hydroxybutyrobetaine | Kegg | (R)-Carnitine | Kegg | L-g-Trimethyl-b-hydroxybutyrobetaine | Generator | L-Γ-trimethyl-β-hydroxybutyrobetaine | Generator | (-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrate | HMDB | (R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide | HMDB | (S)-Carnitine | HMDB | 1-Carnitine | HMDB | 3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium | HMDB | 3-Hydroxy-4-trimethylammoniobutanoate | HMDB | 3-Hydroxy-4-trimethylammoniobutanoic acid | HMDB | Bicarnesine | HMDB | Carniking | HMDB | Carniking 50 | HMDB | Carnilean | HMDB | Carnipass | HMDB | Carnipass 20 | HMDB | D-Carnitine | HMDB | delta-Carnitine | HMDB | DL-Carnitine | HMDB | gamma-Trimethyl-ammonium-beta-hydroxybutirate | HMDB | gamma-Trimethyl-beta-hydroxybutyrobetaine | HMDB | gamma-Trimethyl-hydroxybutyrobetaine | HMDB | L-(-)-Carnitine | HMDB | Levocarnitina | HMDB | Levocarnitinum | HMDB | R-(-)-3-Hydroxy-4-trimethylaminobutyrate | HMDB | L Carnitine | HMDB | L-Carnitine | ChEBI |
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Chemical Formula | C7H15NO3 |
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Average Molecular Weight | 161.1989 |
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Monoisotopic Molecular Weight | 161.105193351 |
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IUPAC Name | (3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate |
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Traditional Name | L-carnitine |
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CAS Registry Number | 541-14-0 |
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SMILES | C[N+](C)(C)C[C@H](O)CC([O-])=O |
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InChI Identifier | InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1 |
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InChI Key | PHIQHXFUZVPYII-ZCFIWIBFSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as carnitines. These are organic compounds containing the quaternary ammonium compound carnitine. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Quaternary ammonium salts |
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Direct Parent | Carnitines |
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Alternative Parents | |
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Substituents | - Carnitine
- Beta-hydroxy acid
- Short-chain hydroxy acid
- Fatty acid
- Hydroxy acid
- Tetraalkylammonium salt
- 1,2-aminoalcohol
- Carboxylic acid salt
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Organooxygen compound
- Organic zwitterion
- Organic salt
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Amine
- Alcohol
- 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 | - Cytoplasm
- Endoplasmic reticulum
- Mitochondria
- Peroxisome
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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 | 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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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9100000000-1b25dacb04c3ed5be8d0 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9100000000-c15eaa190d1e28a4839a | 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 (TMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 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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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-0900000000-9b579c570aab7c7d3a21 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0ik9-0900000000-e37d3def2de1af5bd2f5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0ue9-8900000000-cf37f0a721cd52d86e8e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0r0c-9200000000-a11a4872036f3c33d25a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0a4l-9000000000-2402e260a330ff1772a1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-0w29-6900000000-d0136248acdd706e650b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0ik9-2900000000-61732bb10307f2b183ca | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0zg0-9400000000-15c3db3324f1d46d3c7c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0ik9-2900000000-ee79f10dce9fc09246ec | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01ox-0900000000-3bffd5143cf8b072299e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kf-0900000000-e68f553bcb15d3ef5b47 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-9200000000-c5b43723951af6da48cf | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-1900000000-dd1b1a023937cdcb11af | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-114i-3900000000-9f24d3bc535736149e2a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-632ef17d9dde38586990 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-3900000000-97af6636a917c0edea61 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01pc-9300000000-543e21cb6b9785149e31 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-08fr-9000000000-9128d6fe96d9c7276695 | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
- Mitochondria
- Peroxisome
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Biospecimen Locations | - Adipose Tissue
- Bladder
- Blood
- Brain
- Colostrum
- Erythrocyte
- Fibroblasts
- Heart
- Intestine
- Kidney
- Liver
- Longissimus Thoracis Muscle
- Lung
- Mammary Gland
- Milk
- Muscle
- Neuron
- Placenta
- Platelet
- Prostate Tissue
- Ruminal Fluid
- Semimembranosus Muscle
- Testis
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Pathways | |
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Normal Concentrations |
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Adipose Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Bladder | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 1.29 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 7 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 2.54 +/- 0.51 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 3.14 +/- 0.66 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 6.12 +/- 21.7 uM | Not Specified | Not Specified | Normal | | details | Blood | 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 | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Erythrocyte | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Heart | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 22 +/- 6 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Longissimus Thoracis Muscle | Detected and Quantified | 1856 +/- 424 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Lung | Expected 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 | 346 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 61 +/- 6 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 68 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 68 +/- 5 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 62 +/- 3 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 and Quantified | 81.36 +/- 20.84 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 72.7 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 77 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 79 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 67 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 85.71 +/- 17.08 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 and Quantified | 75.91 +/- 18.17 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 317-437 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 1022.66 +/- 63.87 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 1072.83 +/- 69.97 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 791-1143 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 829.28 +/- 38.28 uM | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 2600 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Muscle | Detected and Quantified | 983.18 +/- 45.99 uM | Not Specified | Not Specified | Normal | | details | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Platelet | 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 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Semimembranosus Muscle | Detected and Quantified | 1751 +/- 337 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 20 +/- 6 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.00 +/- 0 uM | Not Specified | Not Specified | Transition disease/1 wk after parturition | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected and Quantified | 6.34 +/- 1.87 uM | Not Specified | Not Specified | Transition disease/1 wk after parturition | | details | Blood | Detected and Quantified | 6.67 +/- 2.45 uM | Not Specified | Not Specified | Transition disease/1 wk after parturition | | details |
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External Links |
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HMDB ID | HMDB0000062 |
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DrugBank ID | DB00583 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB000571 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 2006614 |
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KEGG Compound ID | C00318 |
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BioCyc ID | CARNITINE |
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BiGG ID | 34600 |
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Wikipedia Link | Carnitine |
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METLIN ID | 52 |
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PubChem Compound | 10917 |
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PDB ID | Not Available |
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ChEBI ID | 16347 |
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References |
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Synthesis Reference | Bols, Mikael; Lundt, Inge; Pedersen, Christian. Simple synthesis of (R)-carnitine from D-galactono-1,4-lactone. Tetrahedron (1992), 48(2), 319-24. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
- Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
- Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
- Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- 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.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
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