Record Information |
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Version | 1.0 |
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Created at | 2022-09-04 18:15:35 UTC |
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Updated at | 2022-09-04 18:15:35 UTC |
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NP-MRD ID | NP0199585 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | α-l-rhamnopyranose |
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Description | α-l-rhamnopyranose is found in Cussonia spicata, Ipomoea muricata, Joannesia princeps, Primula veris and Prunus avium. It was first documented in 2009 (PMID: 19443021). |
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Structure | [H][C@@]1(C)O[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O 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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Synonyms | Value | Source |
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alpha-6-Deoxy-L-mannose | ChEBI | alpha-L-Mannomethylose | ChEBI | alpha-L-Rha | ChEBI | alpha-L-Rhamnose | ChEBI | alpha-L-Rhap | ChEBI | alpha-L-Rhamnopyranose | Kegg | a-6-Deoxy-L-mannose | Generator | Α-6-deoxy-L-mannose | Generator | a-L-Mannomethylose | Generator | Α-L-mannomethylose | Generator | a-L-Rha | Generator | Α-L-rha | Generator | a-L-Rhamnose | Generator | Α-L-rhamnose | Generator | a-L-Rhap | Generator | Α-L-rhap | Generator | a-L-Rhamnopyranose | Generator |
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Chemical Formula | C6H12O5 |
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Average Mass | 164.1565 Da |
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Monoisotopic Mass | 164.06847 Da |
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IUPAC Name | (2R,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol |
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Traditional Name | α-L-rhamnopyranose |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]1(C)O[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O |
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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-HGVZOGFYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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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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Physical Properties |
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State | Not Available |
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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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General References | - von Gunten S, Smith DF, Cummings RD, Riedel S, Miescher S, Schaub A, Hamilton RG, Bochner BS: Intravenous immunoglobulin contains a broad repertoire of anticarbohydrate antibodies that is not restricted to the IgG2 subclass. J Allergy Clin Immunol. 2009 Jun;123(6):1268-76.e15. doi: 10.1016/j.jaci.2009.03.013. Epub 2009 May 13. [PubMed:19443021 ]
- Schneider C, Smith DF, Cummings RD, Boligan KF, Hamilton RG, Bochner BS, Miescher S, Simon HU, Pashov A, Vassilev T, von Gunten S: The human IgG anti-carbohydrate repertoire exhibits a universal architecture and contains specificity for microbial attachment sites. Sci Transl Med. 2015 Jan 7;7(269):269ra1. doi: 10.1126/scitranslmed.3010524. [PubMed:25568069 ]
- Martin CE, Broecker F, Oberli MA, Komor J, Mattner J, Anish C, Seeberger PH: Immunological evaluation of a synthetic Clostridium difficile oligosaccharide conjugate vaccine candidate and identification of a minimal epitope. J Am Chem Soc. 2013 Jul 3;135(26):9713-22. doi: 10.1021/ja401410y. Epub 2013 Jun 24. [PubMed:23795894 ]
- Martin CE, Broecker F, Eller S, Oberli MA, Anish C, Pereira CL, Seeberger PH: Glycan arrays containing synthetic Clostridium difficile lipoteichoic acid oligomers as tools toward a carbohydrate vaccine. Chem Commun (Camb). 2013 Aug 18;49(64):7159-61. doi: 10.1039/c3cc43545h. [PubMed:23836132 ]
- Broecker F, Hanske J, Martin CE, Baek JY, Wahlbrink A, Wojcik F, Hartmann L, Rademacher C, Anish C, Seeberger PH: Multivalent display of minimal Clostridium difficile glycan epitopes mimics antigenic properties of larger glycans. Nat Commun. 2016 Apr 19;7:11224. doi: 10.1038/ncomms11224. [PubMed:27091615 ]
- LOTUS database [Link]
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