Record Information |
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Version | 2.0 |
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Created at | 2024-09-10 19:06:52 UTC |
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Updated at | 2024-09-10 19:06:52 UTC |
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NP-MRD ID | NP0334605 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | N-Acetyl-beta-D-galactosamine |
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Description | N-Acetyl-b-D-galactosamine, also known as beta-galnac or β-galnac, belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. An N-acetyl-D-galactosamine having beta-configuration at the anomeric centre. N-Acetyl-b-D-galactosamine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-b-D-galactosamine exists in all living organisms, ranging from bacteria to humans. Outside of the human body, N-Acetyl-b-D-galactosamine has been detected, but not quantified in, several different foods, such as onion-family vegetables, purple mangosteens, savoy cabbages, common beets, and wax gourds. It was first documented in 1996 (PMID: 8930627). This could make N-acetyl-b-D-galactosamine a potential biomarker for the consumption of these foods (PMID: 12829005) (PMID: 12383482) (PMID: 9732975) (PMID: 19443021) (PMID: 31537530) (PMID: 10732728). |
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Structure | CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1O InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8-/m1/s1 |
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Synonyms | Value | Source |
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2-Acetamido-2-deoxy-beta-D-galactopyranoside | ChEBI | beta-GalNAc | ChEBI | BGalNAc | ChEBI | 2-Acetamido-2-deoxy-b-D-galactopyranoside | Generator | 2-Acetamido-2-deoxy-β-D-galactopyranoside | Generator | b-GalNAc | Generator | Β-galnac | Generator | 2-Deoxy-2-acetamido-b-D-galactopyranose | HMDB | 2-Deoxy-2-acetamido-beta-D-galactopyranose | HMDB | 2-Deoxy-2-acetamido-beta-delta-galactopyranose | HMDB | b-D-2-Acetamido-2-deoxy-galactopyranose | HMDB | b-N-Acetyl-D-galactosamine | HMDB | b-N-Acetylgalactosamine | HMDB | beta-D-2-Acetamido-2-deoxy-galactopyranose | HMDB | beta-delta-2-Acetamido-2-deoxy-galactopyranose | HMDB | beta-N-Acetyl-D-galactosamine | HMDB | beta-N-Acetyl-delta-galactosamine | HMDB | beta-N-Acetylgalactosamine | HMDB | 2 Acetamido 2 D galactopyranose | HMDB | 2-Acetamido-2-deoxy-D-galactose | HMDB | 2 Acetamido 2 deoxy D galactose | HMDB | 2-Acetamido-2-D-galactopyranose | HMDB | Acetylgalactosamine | HMDB | 2 Acetamido 2 deoxygalactose | HMDB | N-Acetyl-D-galactosamine | HMDB | 2-Acetamido-2-deoxygalactose | HMDB | N Acetyl D galactosamine | HMDB | N-Acetyl-β-D-galactosamine | HMDB | N-Acetyl-b-D-galactosamine | Generator |
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Chemical Formula | C8H15NO6 |
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Average Mass | 221.2078 Da |
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Monoisotopic Mass | 221.08994 Da |
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IUPAC Name | N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide |
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Traditional Name | N-acetyl-β-D-galactosamine |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8-/m1/s1 |
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InChI Key | OVRNDRQMDRJTHS-JAJWTYFOSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. |
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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 | N-acyl-alpha-hexosamines |
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Alternative Parents | |
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Substituents | - N-acyl-alpha-hexosamine
- Hexose monosaccharide
- Monosaccharide
- Oxane
- Hemiacetal
- Secondary alcohol
- Carboximidic acid
- Carboximidic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Alcohol
- Organonitrogen compound
- Organic nitrogen compound
- Primary alcohol
- Organopnictogen compound
- Hydrocarbon derivative
- 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 | - Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
- Barbas C, Garcia A, de Miguel L, Simo C: Evaluation of filter paper collection of urine samples for detection and measurement of organic acidurias by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 15;780(1):73-82. [PubMed:12383482 ]
- Garcia A, Barbas C, Aguilar R, Castro M: Capillary electrophoresis for rapid profiling of organic acidurias. Clin Chem. 1998 Sep;44(9):1905-11. [PubMed:9732975 ]
- 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 ]
- Jandus P, Boligan KF, Smith DF, de Graauw E, Grimbacher B, Jandus C, Abdelhafez MM, Despont A, Bovin N, Simon D, Rieben R, Simon HU, Cummings RD, von Gunten S: The architecture of the IgG anti-carbohydrate repertoire in primary antibody deficiencies. Blood. 2019 Nov 28;134(22):1941-1950. doi: 10.1182/blood.2019001705. [PubMed:31537530 ]
- Gheri G, Bryk SG, Taddei G, Moncini D, Noci I: Sugar residues content and distribution in atrophic and hyperplastic postmenopausal human endometrium: lectin histochemistry. Histol Histopathol. 1996 Oct;11(4):861-7. [PubMed:8930627 ]
- Sediva A, Stejskal J, Bartunkova J, Smetana K Jr, Gabius HJ: Detection of alpha(beta)-N-acetyl-D-galactosamine-binding sites in kidney--relation to Henoch-Schonlein-associated IgA nephropathy. Folia Biol (Praha). 1999;45(4):147-50. [PubMed:10732728 ]
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