| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-07 07:19:26 UTC |
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| Updated at | 2022-09-07 07:19:26 UTC |
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| NP-MRD ID | NP0246018 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | legionaminic acid |
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| Description | Legionaminic acid, also known as legionaminate or 5,7-diacnh-tdna, belongs to the class of organic compounds known as pyranoid amino acids and derivatives. Pyranoid amino acids and derivatives are compounds containing a (hydro)pyran ring bearing unprotected amino and carboxylic acid functionalities. legionaminic acid is found in Tannerella forsythia. legionaminic acid was first documented in 2021 (PMID: 34519150). Based on a literature review a small amount of articles have been published on legionaminic acid (PMID: 35420827) (PMID: 34782242) (PMID: 33150386) (PMID: 32886756). |
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| Structure | C[C@@H](O)[C@@H](N)[C@@H]1O[C@@](O)(C[C@H](O)[C@H]1N)C(O)=O InChI=1S/C9H18N2O6/c1-3(12)5(10)7-6(11)4(13)2-9(16,17-7)8(14)15/h3-7,12-13,16H,2,10-11H2,1H3,(H,14,15)/t3-,4+,5-,6-,7+,9+/m1/s1 |
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| Synonyms | | Value | Source |
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| (6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-alpha-L-threo-hex-2-ulopyranosonate | ChEBI | | (6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-a-L-threo-hex-2-ulopyranosonate | Generator | | (6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-a-L-threo-hex-2-ulopyranosonic acid | Generator | | (6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-alpha-L-threo-hex-2-ulopyranosonic acid | Generator | | (6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-α-L-threo-hex-2-ulopyranosonate | Generator | | (6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-α-L-threo-hex-2-ulopyranosonic acid | Generator | | Legionaminate | Generator | | 5,7-DiAcNH-tdna | MeSH | | 5,7-Diacetamido-8-O-acetyl-3,5,7,9-tetradeoxy-glycero-talo-nonulosonic acid | MeSH |
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| Chemical Formula | C9H18N2O6 |
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| Average Mass | 250.2510 Da |
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| Monoisotopic Mass | 250.11649 Da |
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| IUPAC Name | (2S,4S,5R,6S)-5-amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-2,4-dihydroxyoxane-2-carboxylic acid |
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| Traditional Name | (2S,4S,5R,6S)-5-amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-2,4-dihydroxyoxane-2-carboxylic acid |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@@H](O)[C@@H](N)[C@@H]1O[C@@](O)(C[C@H](O)[C@H]1N)C(O)=O |
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| InChI Identifier | InChI=1S/C9H18N2O6/c1-3(12)5(10)7-6(11)4(13)2-9(16,17-7)8(14)15/h3-7,12-13,16H,2,10-11H2,1H3,(H,14,15)/t3-,4+,5-,6-,7+,9+/m1/s1 |
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| InChI Key | ZFZFJUIKYIVPNP-OWTNSLFHSA-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 pyranoid amino acids and derivatives. Pyranoid amino acids and derivatives are compounds containing a (hydro)pyran ring bearing unprotected amino and carboxylic acid functionalities. |
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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 | Pyranoid amino acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Pyranoid amino acid
- C-glucuronide
- Delta amino acid or derivatives
- C-glycosyl compound
- Glycosyl compound
- Amino saccharide
- Alpha-hydroxy acid
- Hydroxy acid
- Oxane
- Pyran
- 1,2-aminoalcohol
- Amino acid or derivatives
- Amino acid
- Hemiacetal
- Secondary alcohol
- Oxacycle
- Carboxylic acid
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Primary aliphatic amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organopnictogen compound
- Alcohol
- Organonitrogen compound
- Primary amine
- Amine
- 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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