| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-11 16:25:08 UTC |
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| Updated at | 2022-05-11 16:25:08 UTC |
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| NP-MRD ID | NP0086582 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid |
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| Description | 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, also known as 2-KDN or 2-keto-3-deoxy-D-glycero-D-galacto-NONONate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). In certain cancers, changes in sialic acid amounts, types, and linkages have been associated with tumorogenesis and cancer metastasis. 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid was first documented in 2000 (PMID: 10749855). Its expression is thought to be regulated by multiple biosynthetic steps catalyzed by several enzymes, including CMP-Sia synthetase (PMID: 11479279). |
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| Structure | OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)CC(=O)C(O)=O InChI=1S/C9H16O9/c10-2-5(13)7(15)8(16)6(14)3(11)1-4(12)9(17)18/h3,5-8,10-11,13-16H,1-2H2,(H,17,18)/t3-,5-,6+,7+,8+/m0/s1 |
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| Synonyms | | Value | Source |
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| 3-Deoxy-D-glycero-D-galacto-2-nonulosonate | Generator | | 2-KDN | HMDB | | 2-Keto-3-deoxy-D-glycero-D-galacto-NONONate | HMDB | | 2-Keto-3-deoxy-D-glycero-D-galacto-NONONic acid | HMDB | | 2-oxo-3-Deoxy-D-glycero-galactononulosonate | HMDB | | 2-oxo-3-Deoxy-D-glycero-galactononulosonic acid | HMDB | | 3-Deoxy-D-glycero-D-galacto-nonulosonate | HMDB | | 3-Deoxy-D-glycero-D-galacto-nonulosonic acid | HMDB | | 3-Deoxyglycero-galacto-nonulosonate | HMDB | | 3-Deoxyglycero-galacto-nonulosonic acid | HMDB | | 3-Deoxyglycerogalacto-2-nonulopyranosonate | HMDB | | 3-Deoxyglycerogalacto-2-nonulopyranosonic acid | HMDB | | Deoxy-KDN | HMDB | | KDN | HMDB | | Sialosonate | HMDB | | Sialosonic acid | HMDB | | SiaX | HMDB | | (4S,5R,6R,7R,8S)-4,5,6,7,8,9-Hexahydroxy-2-oxononanoate | HMDB | | 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid | MeSH |
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| Chemical Formula | C9H16O9 |
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| Average Mass | 268.2179 Da |
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| Monoisotopic Mass | 268.07943 Da |
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| IUPAC Name | (4S,5R,6R,7R,8S)-4,5,6,7,8,9-hexahydroxy-2-oxononanoic acid |
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| Traditional Name | siaX |
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| CAS Registry Number | Not Available |
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| SMILES | OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)CC(=O)C(O)=O |
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| InChI Identifier | InChI=1S/C9H16O9/c10-2-5(13)7(15)8(16)6(14)3(11)1-4(12)9(17)18/h3,5-8,10-11,13-16H,1-2H2,(H,17,18)/t3-,5-,6+,7+,8+/m0/s1 |
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| InChI Key | FQHUAUMYHAJTDH-IMSDGWMTSA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid 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 | Sugar acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Nonose monosaccharide
- Medium-chain keto acid
- Sugar acid
- Alpha-keto acid
- Beta-hydroxy ketone
- Monosaccharide
- Keto acid
- Alpha-hydroxy ketone
- Secondary alcohol
- Ketone
- Polyol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Alcohol
- Carbonyl group
- Primary alcohol
- Hydrocarbon derivative
- Organic oxide
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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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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