| Record Information |
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| Version | 5.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2021-09-14 15:18:17 UTC |
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| HMDB ID | HMDB0001514 |
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| Secondary Accession Numbers | - HMDB0006479
- HMDB0015410
- HMDB01514
- HMDB06479
- HMDB15410
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| Metabolite Identification |
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| Common Name | Glucosamine |
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| Description | Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of two polysaccharides, chitosan and chitin. Glucosamine is one of the most abundant monosaccharides. Produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat, glucosamine has many names depending on country. Although a common dietary supplement, there is little evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug. In the United States, glucosamine is not approved by the Food and Drug Administration for medical use in humans. Since glucosamine is classified as a dietary supplement, evidence of safety and efficacy is not required as long as it is not advertised as a treatment for a medical condition. Nevertheless, glucosamine is a popular alternative medicine used by consumers for the treatment of osteoarthritis. Glucosamine is also extensively used in veterinary medicine as an unregulated but widely accepted supplement. Treatment with oral glucosamine is commonly used for the treatment of osteoarthritis. Since glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage, supplemental glucosamine may help to rebuild cartilage and treat arthritis. However, there is little evidence that any clinical effect of glucosamine works this way. Its use as a therapy for osteoarthritis appears safe but there is conflicting evidence as to its effectiveness. Glucosamine is naturally present in the shells of shellfish, animal bones, bone marrow, and fungi. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars. Specifically in humans, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine by glutamine—fructose-6-phosphate transaminase as the first step of the hexosamine biosynthesis pathway. The end-product of this pathway is uridine diphosphate N-acetylglucosamine (UDP-GlcNAc), which is then used for making glycosaminoglycans, proteoglycans, and glycolipids. As the formation of glucosamine-6-phosphate is the first step for the synthesis of these products, glucosamine may be important in regulating their production; however, the way that the hexosamine biosynthesis pathway is actually regulated, and whether this could be involved in contributing to human disease remains unclear. |
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| Structure | N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1 |
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| Synonyms | | Value | Source |
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| 2-Amino-2-deoxy-D-glucose | ChEBI | | Chitosamine | ChEBI | | D-Glucosamine | ChEBI | | (+)-2-Amino-2-deoxy-D-glucopyranose | HMDB | | (3R,4R,5S,6R)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol | HMDB | | 2-Amino-2-deoxy-D-glucopyranose | HMDB | | 2-Amino-2-deoxyglucose | HMDB | | 2-Aminoglucose | HMDB | | 2-Deoxy-2-amino-D-glucose | HMDB | | 2-Deoxy-2-aminoglucose | HMDB | | Cosamin | HMDB | | D-(+)-Glucosamine | HMDB | | Dona | HMDB | | Fides ecopharma brand OF glucosamine sulfate | HMDB | | Rottapharm brand OF glucosamine sulfate | HMDB | | Xicil | HMDB | | 2 Amino 2 deoxyglucose | HMDB | | Glucosamine sulfate | HMDB | | Sulfate, glucosamine | HMDB | | Dona S | HMDB | | Opfermann brand OF glucosamine sulfate | HMDB | | Hespercorbin | HMDB |
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| Chemical Formula | C6H13NO5 |
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| Average Molecular Weight | 179.1711 |
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| Monoisotopic Molecular Weight | 179.079372531 |
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| IUPAC Name | (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol |
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| Traditional Name | glucosamine |
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| CAS Registry Number | 3416-24-8 |
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| SMILES | N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O |
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| InChI Identifier | InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1 |
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| InChI Key | MSWZFWKMSRAUBD-IVMDWMLBSA-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
- Amino saccharide
- Oxane
- 1,2-aminoalcohol
- Hemiacetal
- Secondary alcohol
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Primary amine
- Primary alcohol
- Organopnictogen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organic nitrogen compound
- Alcohol
- Amine
- Hydrocarbon derivative
- 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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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | 88 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 330 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Spectral Properties | Collision Cross SectionsRetention IndicesUnderivatizedNot Available Derivatized| Derivative | Value | Reference |
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| Glucosamine,1TMS,#1 | 1764.1383 | https://arxiv.org/abs/1905.12712 | | Glucosamine,1TMS,#2 | 1785.958 | https://arxiv.org/abs/1905.12712 | | Glucosamine,1TMS,#3 | 1785.5004 | https://arxiv.org/abs/1905.12712 | | Glucosamine,1TMS,#4 | 1779.1104 | https://arxiv.org/abs/1905.12712 | | Glucosamine,1TMS,#5 | 1814.2131 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TMS,#1 | 1769.5471 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TMS,#2 | 1759.951 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TMS,#3 | 1755.7238 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TMS,#4 | 1803.0923 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TMS,#5 | 1777.8608 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TMS,#6 | 1768.2544 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TMS,#7 | 1812.1799 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TMS,#8 | 1733.0703 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TMS,#9 | 1808.6088 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TMS,#10 | 1797.4208 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TMS,#11 | 1906.6954 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#1 | 1821.0793 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#2 | 1799.998 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#3 | 1807.1201 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#4 | 1807.2786 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#5 | 1833.9231 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#6 | 1829.1854 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#7 | 1937.1545 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#8 | 1786.8485 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#9 | 1834.7787 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#10 | 1837.0623 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#11 | 1950.662 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#12 | 1832.4022 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#13 | 1929.2059 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TMS,#14 | 1912.4023 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TMS,#1 | 1841.2505 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TMS,#2 | 1906.8885 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TMS,#3 | 1907.1149 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TMS,#4 | 1926.5023 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TMS,#5 | 1891.7167 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TMS,#6 | 1963.9908 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TMS,#7 | 1964.6593 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TMS,#8 | 1906.7488 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TMS,#9 | 1946.811 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TMS,#10 | 1954.4313 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TMS,#11 | 1932.0774 | https://arxiv.org/abs/1905.12712 | | Glucosamine,1TBDMS,#1 | 2014.064 | https://arxiv.org/abs/1905.12712 | | Glucosamine,1TBDMS,#2 | 2058.599 | https://arxiv.org/abs/1905.12712 | | Glucosamine,1TBDMS,#3 | 2034.4552 | https://arxiv.org/abs/1905.12712 | | Glucosamine,1TBDMS,#4 | 2026.4412 | https://arxiv.org/abs/1905.12712 | | Glucosamine,1TBDMS,#5 | 2109.6577 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TBDMS,#1 | 2237.4246 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TBDMS,#2 | 2244.3726 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TBDMS,#3 | 2228.6995 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TBDMS,#4 | 2280.321 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TBDMS,#5 | 2257.803 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TBDMS,#6 | 2237.0667 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TBDMS,#7 | 2300.9463 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TBDMS,#8 | 2221.9668 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TBDMS,#9 | 2289.085 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TBDMS,#10 | 2272.0725 | https://arxiv.org/abs/1905.12712 | | Glucosamine,2TBDMS,#11 | 2368.243 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#1 | 2477.7273 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#2 | 2464.5476 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#3 | 2505.0884 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#4 | 2461.6514 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#5 | 2525.7788 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#6 | 2513.2124 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#7 | 2595.4453 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#8 | 2467.1733 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#9 | 2536.2834 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#10 | 2539.2004 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#11 | 2630.247 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#12 | 2524.8564 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#13 | 2610.646 | https://arxiv.org/abs/1905.12712 | | Glucosamine,3TBDMS,#14 | 2594.1191 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TBDMS,#1 | 2694.8313 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TBDMS,#2 | 2731.4492 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TBDMS,#3 | 2739.54 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TBDMS,#4 | 2828.967 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TBDMS,#5 | 2716.0596 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TBDMS,#6 | 2857.1804 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TBDMS,#7 | 2842.742 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TBDMS,#8 | 2750.878 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TBDMS,#9 | 2845.0562 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TBDMS,#10 | 2873.4958 | https://arxiv.org/abs/1905.12712 | | Glucosamine,4TBDMS,#11 | 2839.106 | https://arxiv.org/abs/1905.12712 |
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| GC-MS| Spectrum Type | Description | Splash Key | Deposition Date | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-06tr-9300000000-7e2a89f48724cdda814c | 2017-09-01 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-0ul9-9847700000-b4779809586433e7ec78 | 2017-10-06 | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-06tr-9300000000-7e2a89f48724cdda814c | 2021-09-05 | View Spectrum |
LC-MS/MS| Spectrum Type | Description | Splash Key | Deposition Date | View |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-4900000000-364d52fc6e7e423f52bb | 2018-05-25 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-762e016c89a40a9e3f49 | 2018-05-25 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-9000000000-bd04d561d78f2abad229 | 2018-05-25 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-03di-9500000000-9bfc2897a4b66f71c7a1 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0007-9000000000-f842b779439be8970cd9 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-074i-9000000000-622ec0743231c0cbaca6 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-03e9-9700000000-5087af92679b2640ba6c | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-b9ba212915cbdaed8628 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-2d1825b518f09745e036 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-03la-9100000000-3da7ee17d7512a59e3ef | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-03e9-9400000000-cca17ef05a47a7be4d43 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-01x0-9500000000-5fbd02d318d3ec58f98b | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0abc-9000000000-11e86d324c183174364e | 2021-09-20 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01q9-0900000000-4c88765919efa0ec2d2d | 2016-08-02 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03ea-6900000000-301590fbe90692448d5e | 2016-08-02 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052g-9100000000-d6a51790ce1df14a067a | 2016-08-02 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-002r-9400000000-e43a7a5cb44f6c461544 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-053r-9800000000-56b95ef43b164db5524d | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-1434c5ce1e9649c1cbf1 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01ox-0900000000-400a58d3fc54c3aaa598 | 2021-09-08 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-022c-9100000000-a61fa7431c3bb2a108d9 | 2021-09-08 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-9d850e653d9a1cc1e5ee | 2021-09-08 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-9300000000-6c60a7f332602832baaf | 2021-09-08 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-9200000000-77db29658fe1def3600e | 2021-09-08 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-bd64268dc67588fc1969 | 2021-09-08 | View Spectrum |
NMR| Spectrum Type | Description | Deposition Date | View |
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| 2D NMR | [1H, 1H] 2D NMR Spectrum (predicted) | 2018-05-25 | View Spectrum | | 2D NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted) | 2018-05-25 | View Spectrum |
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| General References | - Thatte HS, Zagarins S, Khuri SF, Fischer TH: Mechanisms of poly-N-acetyl glucosamine polymer-mediated hemostasis: platelet interactions. J Trauma. 2004 Jul;57(1 Suppl):S13-21. [PubMed:15280745 ]
- Ruoslahti E, Engvall E, Hayman EG, Spiro RG: Comparative studies on amniotic fluid and plasma fibronectins. Biochem J. 1981 Jan 1;193(1):295-9. [PubMed:7305927 ]
- Rhodes M, Allen A, Dowling RH, Murphy G, Lennard TW: Inhibition of human gall bladder mucus synthesis in patients undergoing cholecystectomy. Gut. 1992 Aug;33(8):1113-7. [PubMed:1398238 ]
- Cibere J, Thorne A, Kopec JA, Singer J, Canvin J, Robinson DB, Pope J, Hong P, Grant E, Lobanok T, Ionescu M, Poole AR, Esdaile JM: Glucosamine sulfate and cartilage type II collagen degradation in patients with knee osteoarthritis: randomized discontinuation trial results employing biomarkers. J Rheumatol. 2005 May;32(5):896-902. [PubMed:15868627 ]
- Morita H, Kettlewell MG, Jewell DP, Kent PW: Glycosylation and sulphation of colonic mucus glycoproteins in patients with ulcerative colitis and in healthy subjects. Gut. 1993 Jul;34(7):926-32. [PubMed:8344580 ]
- Zhang LJ, Huang TM, Fang XL, Li XN, Wang QS, Zhang ZW, Sha XY: Determination of glucosamine sulfate in human plasma by precolumn derivatization using high performance liquid chromatography with fluorescence detection: its application to a bioequivalence study. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Sep 14;842(1):8-12. Epub 2006 Jun 5. [PubMed:16740419 ]
- Hoffer LJ, Kaplan LN, Hamadeh MJ, Grigoriu AC, Baron M: Sulfate could mediate the therapeutic effect of glucosamine sulfate. Metabolism. 2001 Jul;50(7):767-70. [PubMed:11436179 ]
- Huang TM, Cai L, Yang B, Zhou MX, Shen YF, Duan GL: Liquid chromatography with electrospray ionization mass spectrometry method for the assay of glucosamine sulfate in human plasma: validation and application to a pharmacokinetic study. Biomed Chromatogr. 2006 Mar;20(3):251-6. [PubMed:16145658 ]
- Biggee BA, Blinn CM, McAlindon TE, Nuite M, Silbert JE: Low levels of human serum glucosamine after ingestion of glucosamine sulphate relative to capability for peripheral effectiveness. Ann Rheum Dis. 2006 Feb;65(2):222-6. Epub 2005 Aug 3. [PubMed:16079170 ]
- McCarty MF: Enhanced synovial production of hyaluronic acid may explain rapid clinical response to high-dose glucosamine in osteoarthritis. Med Hypotheses. 1998 Jun;50(6):507-10. [PubMed:9710325 ]
- Uitterlinden EJ, Jahr H, Koevoet JL, Jenniskens YM, Bierma-Zeinstra SM, Degroot J, Verhaar JA, Weinans H, van Osch GJ: Glucosamine decreases expression of anabolic and catabolic genes in human osteoarthritic cartilage explants. Osteoarthritis Cartilage. 2006 Mar;14(3):250-7. Epub 2005 Nov 18. [PubMed:16300972 ]
- Cope GF, Heatley RV, Kelleher J, Axon AT: In vitro mucus glycoprotein production by colonic tissue from patients with ulcerative colitis. Gut. 1988 Feb;29(2):229-34. [PubMed:3345934 ]
- McCarty MF: Glucosamine may retard atherogenesis by promoting endothelial production of heparan sulfate proteoglycans. Med Hypotheses. 1997 Mar;48(3):245-51. [PubMed:9140889 ]
- Cheung HS, Nicoloff JT, Kamiel MB, Spolter L, Nimni ME: Stimulation of fibroblast biosynthetic activity by serum of patients with pretibial myxedema. J Invest Dermatol. 1978 Jul;71(1):12-7. [PubMed:355562 ]
- Valeri CR, Srey R, Tilahun D, Ragno G: In vitro effects of poly-N-acetyl glucosamine on the activation of platelets in platelet-rich plasma with and without red blood cells. J Trauma. 2004 Jul;57(1 Suppl):S22-5; discussion S25. [PubMed:15280746 ]
- Roseman S: Reflections on glycobiology. J Biol Chem. 2001 Nov 9;276(45):41527-42. Epub 2001 Sep 11. [PubMed:11553646 ]
- GHOSH S, BLUMENTHAL HJ, DAVIDSON E, ROSEMAN S: Glucosamine metabolism. V. Enzymatic synthesis of glucosamine 6-phosphate. J Biol Chem. 1960 May;235:1265-73. [PubMed:13827775 ]
- Laverty S, Sandy JD, Celeste C, Vachon P, Marier JF, Plaas AH: Synovial fluid levels and serum pharmacokinetics in a large animal model following treatment with oral glucosamine at clinically relevant doses. Arthritis Rheum. 2005 Jan;52(1):181-91. [PubMed:15641100 ]
- Towheed TE, Maxwell L, Anastassiades TP, Shea B, Houpt J, Robinson V, Hochberg MC, Wells G: Glucosamine therapy for treating osteoarthritis. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD002946. [PubMed:15846645 ]
- Buse MG: Hexosamines, insulin resistance, and the complications of diabetes: current status. Am J Physiol Endocrinol Metab. 2006 Jan;290(1):E1-E8. [PubMed:16339923 ]
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