| Record Information |
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| Version | 4.0 |
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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 | 2019-07-23 05:44:56 UTC |
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| HMDB ID | HMDB0001367 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | N-Acetyl-glucosamine 1-phosphate |
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| Description | N-Acetyl-glucosamine 1-phosphate, also known as glcnac-1-phosphate, 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. A N-acetyl-N-Acetyl-glucosamine 1-phosphate that is 2-deoxy-D-glucopyranose 1-(dihydrogen phosphate) substituted by an acetamido group at position 2. N-Acetyl-glucosamine 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-glucosamine 1-phosphate exists in all eukaryotes, ranging from yeast to humans. Within humans, N-acetyl-glucosamine 1-phosphate participates in a number of enzymatic reactions. In particular, N-acetyl-glucosamine 1-phosphate can be biosynthesized from N-acetyl-D-glucosamine 6-phosphate through its interaction with the enzyme phosphoacetylglucosamine mutase. In addition, N-acetyl-glucosamine 1-phosphate and uridine triphosphate can be converted into uridine diphosphate-N-acetylglucosamine through its interaction with the enzyme UDP-N-acetylhexosamine pyrophosphorylase. In humans, N-acetyl-glucosamine 1-phosphate is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2-(Acetylamino)-2-deoxy-D-glucopyranose 1-(dihydrogen phosphate) | ChEBI | | 2-Acetamido-2-deoxy-1-O-phosphono-D-glucopyranose | ChEBI | | N-Acetyl-D-glucosamine 1-phosphate | ChEBI | | N-Acetylglucosamine-1-phosphate | ChEBI | | 2-(Acetylamino)-2-deoxy-D-glucopyranose 1-(dihydrogen phosphoric acid) | Generator | | N-Acetyl-D-glucosamine 1-phosphoric acid | Generator | | N-Acetylglucosamine-1-phosphoric acid | Generator | | N-Acetyl-glucosamine 1-phosphoric acid | Generator | | D-Glucosamine 1-phosphate | HMDB | | delta-Glucosamine 1-phosphate | HMDB | | N-Acetyl-alpha-D-glucosamine 1-phosphate | HMDB | | N-Acetyl-alpha-delta-glucosamine 1-phosphate | HMDB | | N-Acetyl-delta-glucosamine 1-phosphate | HMDB | | N-Acetyl-glucosamine-1-phosphate | HMDB | | GlcNAc-1-phosphate | HMDB |
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| Chemical Formula | C8H16NO9P |
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| Average Molecular Weight | 301.1877 |
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| Monoisotopic Molecular Weight | 301.056267627 |
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| IUPAC Name | {[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid |
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| Traditional Name | [(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid |
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| CAS Registry Number | 6866-69-9 |
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| SMILES | CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OP(O)(O)=O |
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| InChI Identifier | InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/t4-,5-,6-,7-,8?/m1/s1 |
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| InChI Key | FZLJPEPAYPUMMR-RTRLPJTCSA-N |
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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 phosphate
- Monoalkyl phosphate
- Monosaccharide
- Organic phosphoric acid derivative
- Oxane
- Phosphoric acid ester
- Alkyl phosphate
- Acetamide
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Primary alcohol
- Carbonyl group
- Organonitrogen compound
- Organic oxide
- Alcohol
- Organopnictogen compound
- Organic nitrogen 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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| Ontology |
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| Disposition | Source: Biological location: |
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| Process | Naturally occurring process: |
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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 | 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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| | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-007k-9230000000-37cdd3ef185356d03c19 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0f6t-9211240000-817e06893a2ccced098b | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-1094000000-f1e04aaf05d431b8b0ab | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f7k-6290000000-6ff96a8c8bf54d5e8bfa | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f6t-9620000000-3e2ee2ffc3801abdb7da | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-002s-9211000000-7f3631860a58ca188060 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9110000000-9614f2b717f8fb17cc08 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-1a4f6aa02a49053d5b95 | JSpectraViewer |
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