Record Information |
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Version | 1.0 |
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Created at | 2022-04-29 01:09:56 UTC |
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Updated at | 2022-04-29 01:09:56 UTC |
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NP-MRD ID | NP0080103 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Thornasteroside A |
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Description | [(2R,5S,7S,8R,10R,11R,14S,15R)-8-{[(2R,3S,4S,5R,6R)-4-{[(2R,3R,4R,5R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-14-[(2R)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(17)-en-5-yl]oxidanesulfonic acid belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. Thornasteroside A is found in Luidia quinaria. Based on a literature review very few articles have been published on [(2R,5S,7S,8R,10R,11R,14S,15R)-8-{[(2R,3S,4S,5R,6R)-4-{[(2R,3R,4R,5R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-14-[(2R)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(17)-en-5-yl]oxidanesulfonic acid. |
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Structure | CC(C)CC(=O)C[C@@](C)(O)[C@H]1CC[C@@H]2[C@H]3C[C@@H](O[C@@H]4O[C@H](C)[C@@H](O)[C@H](O[C@H]5OC[C@@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]6O[C@H]6O[C@H](C)[C@H](O)[C@@H](O)[C@@H]6O)[C@@H](O)[C@H]5O[C@@H]5O[C@H](C)[C@@H](O)[C@H](O)[C@@H]5O)[C@@H]4O)[C@H]4C[C@H](CC[C@@]4(C)C3=CC[C@@]12C)OS(O)(=O)=O InChI=1S/C56H92O28S/c1-21(2)15-25(58)18-56(8,70)34-10-9-28-27-17-31(30-16-26(84-85(71,72)73)11-13-54(30,6)29(27)12-14-55(28,34)7)78-51-45(69)46(37(61)24(5)77-51)81-52-47(82-49-43(67)40(64)35(59)22(3)75-49)39(63)33(20-74-52)80-53-48(42(66)38(62)32(19-57)79-53)83-50-44(68)41(65)36(60)23(4)76-50/h12,21-24,26-28,30-53,57,59-70H,9-11,13-20H2,1-8H3,(H,71,72,73)/t22-,23-,24-,26+,27-,28-,30-,31-,32-,33-,34+,35-,36+,37-,38-,39-,40+,41-,42-,43+,44+,45+,46+,47-,48-,49+,50-,51+,52-,53+,54+,55-,56-/m1/s1 |
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Synonyms | Value | Source |
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[(2R,5S,7S,8R,10R,11R,14S,15R)-8-{[(2R,3S,4S,5R,6R)-4-{[(2R,3R,4R,5R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-14-[(2R)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-1(17)-en-5-yl]oxidanesulfonate | Generator | [(2R,5S,7S,8R,10R,11R,14S,15R)-8-{[(2R,3S,4S,5R,6R)-4-{[(2R,3R,4R,5R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-14-[(2R)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-1(17)-en-5-yl]oxidanesulphonate | Generator | [(2R,5S,7S,8R,10R,11R,14S,15R)-8-{[(2R,3S,4S,5R,6R)-4-{[(2R,3R,4R,5R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-14-[(2R)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-1(17)-en-5-yl]oxidanesulphonic acid | Generator |
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Chemical Formula | C56H92O28S |
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Average Mass | 1245.3800 Da |
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Monoisotopic Mass | 1244.54958 Da |
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IUPAC Name | [(2R,5S,7S,8R,10R,11R,14S,15R)-8-{[(2R,3S,4S,5R,6R)-4-{[(2R,3R,4R,5R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-14-[(2R)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(17)-en-5-yl]oxidanesulfonic acid |
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Traditional Name | [(2R,5S,7S,8R,10R,11R,14S,15R)-8-{[(2R,3S,4S,5R,6R)-4-{[(2R,3R,4R,5R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-3-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-14-[(2R)-2-hydroxy-6-methyl-4-oxoheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(17)-en-5-yl]oxidanesulfonic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(C)CC(=O)C[C@@](C)(O)[C@H]1CC[C@@H]2[C@H]3C[C@@H](O[C@@H]4O[C@H](C)[C@@H](O)[C@H](O[C@H]5OC[C@@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]6O[C@H]6O[C@H](C)[C@H](O)[C@@H](O)[C@@H]6O)[C@@H](O)[C@H]5O[C@@H]5O[C@H](C)[C@@H](O)[C@H](O)[C@@H]5O)[C@@H]4O)[C@H]4C[C@H](CC[C@@]4(C)C3=CC[C@@]12C)OS(O)(=O)=O |
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InChI Identifier | InChI=1S/C56H92O28S/c1-21(2)15-25(58)18-56(8,70)34-10-9-28-27-17-31(30-16-26(84-85(71,72)73)11-13-54(30,6)29(27)12-14-55(28,34)7)78-51-45(69)46(37(61)24(5)77-51)81-52-47(82-49-43(67)40(64)35(59)22(3)75-49)39(63)33(20-74-52)80-53-48(42(66)38(62)32(19-57)79-53)83-50-44(68)41(65)36(60)23(4)76-50/h12,21-24,26-28,30-53,57,59-70H,9-11,13-20H2,1-8H3,(H,71,72,73)/t22-,23-,24-,26+,27-,28-,30-,31-,32-,33-,34+,35-,36+,37-,38-,39-,40+,41-,42-,43+,44+,45+,46+,47-,48-,49+,50-,51+,52-,53+,54+,55-,56-/m1/s1 |
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InChI Key | FBHHBSPWVXPYPG-NYBHBNACSA-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 steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Steroidal glycosides |
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Direct Parent | Steroidal glycosides |
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Alternative Parents | |
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Substituents | - Diterpene glycoside
- Cholestane-skeleton
- Steroidal glycoside
- Oligosaccharide
- 23-oxosteroid
- Monohydroxy bile acid, alcohol, or derivatives
- Hydroxy bile acid, alcohol, or derivatives
- Bile acid, alcohol, or derivatives
- Sulfated steroid skeleton
- 20-hydroxysteroid
- Diterpenoid
- Oxosteroid
- Hydroxysteroid
- Terpene glycoside
- O-glycosyl compound
- Glycosyl compound
- Sulfuric acid ester
- Alkyl sulfate
- Sulfate-ester
- Sulfuric acid monoester
- Oxane
- Beta-hydroxy ketone
- Tertiary alcohol
- Organic sulfuric acid or derivatives
- Secondary alcohol
- Ketone
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Acetal
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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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