| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-10 01:21:58 UTC |
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| Updated at | 2022-09-10 01:21:59 UTC |
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| NP-MRD ID | NP0293388 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (3s)-n-[(2r,3r,4s,5r,6r)-2-{[(3as,7r,7as)-4,7-dihydroxy-3h,3ah,6h,7h,7ah-imidazo[4,5-c]pyridin-2-yl]amino}-4-hydroxy-5-(c-hydroxycarbonimidoyloxy)-6-(hydroxymethyl)oxan-3-yl]-3,6-diaminohexanimidic acid |
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| Description | Streptothricin F, also known as racemomycin a or yazumycin a, belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). (3s)-n-[(2r,3r,4s,5r,6r)-2-{[(3as,7r,7as)-4,7-dihydroxy-3h,3ah,6h,7h,7ah-imidazo[4,5-c]pyridin-2-yl]amino}-4-hydroxy-5-(c-hydroxycarbonimidoyloxy)-6-(hydroxymethyl)oxan-3-yl]-3,6-diaminohexanimidic acid is found in Streptomyces griseochromogenes, Streptomyces griseus, Streptomyces lavendulae, Streptomyces nojiriensis, Streptomyces qinlingensis and Streptomyces roseolilacinus. (3s)-n-[(2r,3r,4s,5r,6r)-2-{[(3as,7r,7as)-4,7-dihydroxy-3h,3ah,6h,7h,7ah-imidazo[4,5-c]pyridin-2-yl]amino}-4-hydroxy-5-(c-hydroxycarbonimidoyloxy)-6-(hydroxymethyl)oxan-3-yl]-3,6-diaminohexanimidic acid was first documented in 2006 (PMID: 16641084). Based on a literature review very few articles have been published on streptothricin F (PMID: 19897889). |
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| Structure | NCCC[C@H](N)CC(O)=N[C@H]1[C@H](NC2=N[C@H]3[C@H](N2)C(O)=NC[C@H]3O)O[C@H](CO)[C@H](OC(O)=N)[C@H]1O InChI=1S/C19H34N8O8/c20-3-1-2-7(21)4-10(30)24-13-14(31)15(35-18(22)33)9(6-28)34-17(13)27-19-25-11-8(29)5-23-16(32)12(11)26-19/h7-9,11-15,17,28-29,31H,1-6,20-21H2,(H2,22,33)(H,23,32)(H,24,30)(H2,25,26,27)/t7-,8+,9+,11+,12-,13+,14-,15-,17+/m0/s1 |
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| Synonyms | | Value | Source |
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| Antibiotic S 15-1a | ChEBI | | Racemomycin a | ChEBI | | Streptothricin | ChEBI | | Streptothricin VI | ChEBI | | Yazumycin a | ChEBI | | S15-1-a | MeSH |
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| Chemical Formula | C19H34N8O8 |
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| Average Mass | 502.5290 Da |
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| Monoisotopic Mass | 502.24996 Da |
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| IUPAC Name | (3S)-N-[(2R,3R,4S,5R,6R)-2-{[(3aS,7R,7aS)-4,7-dihydroxy-3H,3aH,6H,7H,7aH-imidazo[4,5-c]pyridin-2-yl]amino}-4-hydroxy-5-(C-hydroxycarbonimidoyloxy)-6-(hydroxymethyl)oxan-3-yl]-3,6-diaminohexanimidic acid |
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| Traditional Name | (3S)-N-[(2R,3R,4S,5R,6R)-2-{[(3aS,7R,7aS)-4,7-dihydroxy-3H,3aH,6H,7H,7aH-imidazo[4,5-c]pyridin-2-yl]amino}-4-hydroxy-5-(C-hydroxycarbonimidoyloxy)-6-(hydroxymethyl)oxan-3-yl]-3,6-diaminohexanimidic acid |
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| CAS Registry Number | Not Available |
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| SMILES | NCCC[C@H](N)CC(O)=N[C@H]1[C@H](NC2=N[C@H]3[C@H](N2)C(O)=NC[C@H]3O)O[C@H](CO)[C@H](OC(O)=N)[C@H]1O |
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| InChI Identifier | InChI=1S/C19H34N8O8/c20-3-1-2-7(21)4-10(30)24-13-14(31)15(35-18(22)33)9(6-28)34-17(13)27-19-25-11-8(29)5-23-16(32)12(11)26-19/h7-9,11-15,17,28-29,31H,1-6,20-21H2,(H2,22,33)(H,23,32)(H,24,30)(H2,25,26,27)/t7-,8+,9+,11+,12-,13+,14-,15-,17+/m0/s1 |
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| InChI Key | NRAUADCLPJTGSF-VLSXYIQESA-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 glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). |
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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 | Glycosylamines |
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| Alternative Parents | |
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| Substituents | - Hexose monosaccharide
- Beta amino acid or derivatives
- N-glycosyl compound
- Alpha-amino acid or derivatives
- Imidazopyridine
- Delta-lactam
- Piperidinone
- Fatty amide
- Fatty acyl
- Monosaccharide
- N-acyl-amine
- Oxane
- Piperidine
- 2-imidazoline
- Carbamic acid ester
- Amino acid or derivatives
- Carboxamide group
- Guanidine
- Lactam
- Carbonic acid derivative
- Secondary carboxylic acid amide
- Secondary alcohol
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Carboxylic acid derivative
- Organic 1,3-dipolar compound
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Primary alcohol
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Amine
- Primary aliphatic amine
- Alcohol
- Organonitrogen compound
- Organopnictogen compound
- Carbonyl group
- Primary amine
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic 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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