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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:20:31 UTC |
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Update Date | 2020-06-04 20:32:35 UTC |
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BMDB ID | BMDB0000174 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | L-Fucose |
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Description | L-Fucose, also known as L-rha or 6-deoxymannose, 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. L-Fucose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. L-Fucose exists in all living organisms, ranging from bacteria to humans. L-Fucose can be converted into fucose 1-phosphate; which is mediated by the enzyme L-fucose kinase. In cattle, L-fucose 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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6-Deoxy-L-galactose | ChEBI | (-)-Fucose | HMDB | (-)-L-Fucose | HMDB | 6-Deoxy-L-galactopyranose | HMDB | 6-Desoxygalactose | HMDB | 6-Methyloxane-2,3,4,5-tetrol | HMDB | 6-Methyltetrahydropyran-2,3,4,5-tetraol | HMDB | Fucose | HMDB | Isodulcit | HMDB | L-(-)-Fucose | HMDB | L-Fucopyranose | HMDB | L-Galactomethylose | HMDB | Rhodeose | HMDB | alpha Fucose | HMDB | alpha-Fucose | HMDB | Deoxygalactose | HMDB |
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Chemical Formula | C6H12O5 |
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Average Molecular Weight | 164.1565 |
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Monoisotopic Molecular Weight | 164.068473494 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 2438-80-4 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1 |
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InChI Key | SHZGCJCMOBCMKK-DHVFOXMCSA-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
- 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
- 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 | 140 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 985 mg/mL | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Lysosome
- Myelin sheath
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Biospecimen Locations | - Epidermis
- Fibroblasts
- Intestine
- Kidney
- Liver
- Mammary Gland
- Milk
- Neuron
- Ovary
- Pancreas
- Placenta
- Ruminal Fluid
- Spleen
- Testis
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Pathways | |
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Normal Concentrations |
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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 | 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 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 | 27.79 +/- 13.14 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 35 +/- 9 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 23 +/- 11 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 28 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 25 +/- 3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21.03 +/- 14.33 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 25 +/- 3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 35 +/- 9 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 23 +/- 11 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 28 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 15.36 +/- 7.37 uM | Not Specified | Not Specified | Normal | | details | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ovary | 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 | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 763.813 +/- 751.731 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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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 | HMDB0000174 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB020543 |
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KNApSAcK ID | C00035100 |
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Chemspider ID | 16190 |
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KEGG Compound ID | C01019 |
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BioCyc ID | L-FUCOSE |
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BiGG ID | 36636 |
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Wikipedia Link | Fucose |
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METLIN ID | 268 |
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PubChem Compound | 17106 |
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PDB ID | 1AH1 |
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ChEBI ID | 2181 |
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References |
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Synthesis Reference | Xu, Zuhong; Zhao, Zengqin; Zhang, Quanbin; Niu, Xizhen; Zhang, Hong; Li, Zhien. Method for preparing L-fucose from laminaria japonica. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - 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 ]
- 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 ]
- 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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