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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:20:28 UTC |
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Update Date | 2020-06-04 20:51:47 UTC |
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BMDB ID | BMDB0000169 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | D-Mannose |
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Description | D-Mannose, also known as mannopyranose or carubinose, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. D-Mannose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Mannose exists in all living species, ranging from bacteria to humans. D-Mannose can be converted into mannose 6-phosphate; which is mediated by the enzyme hexokinase-1. In cattle, D-mannose is involved in the metabolic pathway called the fructose and mannose degradation pathway. |
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Structure | |
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Synonyms | Value | Source |
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Carubinose | ChEBI | Mannopyranose | ChEBI | Seminose | ChEBI | Mannose | Kegg | D-Mannopyranose | Kegg | (+)-Mannose | HMDB | (+-)-Mannose | HMDB | D(+)-Mannose | HMDB | DL-Mannose | HMDB | Mannopyranoside | HMDB | D Mannose | HMDB |
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Chemical Formula | C6H12O6 |
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Average Molecular Weight | 180.1559 |
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Monoisotopic Molecular Weight | 180.063388116 |
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IUPAC Name | (3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol |
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Traditional Name | β-glucose |
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CAS Registry Number | 3458-28-4 |
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SMILES | OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1 |
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InChI Key | WQZGKKKJIJFFOK-QTVWNMPRSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Hexoses |
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Alternative Parents | |
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Substituents | - Hexose monosaccharide
- Oxane
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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
- Golgi
- Lysosome
- Myelin sheath
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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 | 132 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 713.0 mg/mL at 17 °C | 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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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS) | splash10-0mi2-0931000000-96f0cf3c2d4a8bea25b9 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS) | splash10-00kb-1931000000-ec423f92582012821c6a | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS) | splash10-0fr2-1920000000-b6be17dc79a948dfe5fa | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX) | splash10-00di-9831000000-409527d22fb759cb628f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX) | splash10-00di-9621000000-34b421fd962840bfbaec | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS) | splash10-066r-1942000000-1c8164b54d2d16c782c3 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS) | splash10-0ldi-1942000000-c68a088eba727f3a4ada | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0mi2-0931000000-96f0cf3c2d4a8bea25b9 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00kb-1931000000-ec423f92582012821c6a | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0fr2-1920000000-b6be17dc79a948dfe5fa | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9831000000-409527d22fb759cb628f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9621000000-34b421fd962840bfbaec | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-066r-1942000000-1c8164b54d2d16c782c3 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0ldi-1942000000-c68a088eba727f3a4ada | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0np0-9700000000-e8d638dc817e46b97d7b | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive | splash10-004i-6122690000-eaf6f7adf34ccd0c667b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-01pc-6900000000-0ef33e32ee16b7803f1b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00kr-9000000000-27e169c1df0c3ee59806 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-03ea-0900000000-9fb0e8db39598c7a269b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01q9-0900000000-b0bc47623e7b2ca31c02 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03ea-3900000000-648e1637af29cf2a3518 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0007-9200000000-9e6f46a1cbf52d6e347a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-2900000000-a4ec4f0b1e29e360a952 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01t9-6900000000-7b3ea9c64ecc8d4ac867 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9100000000-ec2bf4918640a0a36398 | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 22.53 MHz, D2O, experimental) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
- Golgi
- Lysosome
- Myelin sheath
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Biospecimen Locations | - Adrenal Medulla
- Bladder
- Blood
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Liver
- Milk
- Muscle
- Neuron
- Pancreas
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Spleen
- Testis
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Pathways | |
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Normal Concentrations |
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Adrenal Medulla | 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 but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Epidermis | 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 | 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 but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Pancreas | 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 | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 91 +/- 49 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 159 +/- 83 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 211 +/- 86 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 125 +/- 25 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 125 +/- 25 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 91.3 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 159.1 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 210.9 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 123.6 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 763.813 +/- 751.731 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 91.62 +/- 25.1 uM | Not Specified | Not Specified | Normal | | details | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Testis | 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 | 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 but not Quantified | Not Quantified | Not Specified | Not Specified | Mycobacterium avium subsp. paratuberculosis infection | | details | Ruminal Fluid | Detected and Quantified | 210.97 +/- 83.15 uM | Not Specified | Not Specified | Rumen acidosis | | details | Ruminal Fluid | Detected and Quantified | 2415.813 +/- 1248.434 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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External Links |
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HMDB ID | HMDB0000169 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB001202 |
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KNApSAcK ID | C00001126 |
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Chemspider ID | 17893 |
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KEGG Compound ID | C00159 |
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BioCyc ID | MANNOSE |
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BiGG ID | 34085 |
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Wikipedia Link | Mannose |
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METLIN ID | Not Available |
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PubChem Compound | 18950 |
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PDB ID | Not Available |
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ChEBI ID | 4208 |
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References |
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Synthesis Reference | Sowden, John C.; Fischer, Hermann O. L. Condensation of nitromethane with D- and L-arabinose: preparation of L-glucose and L-mannose. Journal of the American Chemical Society (1947), 69 1963-5. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]
- 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.
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.
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