| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-29 01:21:20 UTC |
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| Updated at | 2022-04-29 01:21:20 UTC |
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| NP-MRD ID | NP0080318 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Versicoside A |
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| Description | [(2R,5S,7R,8R,10R,11R,14R,15R)-8-{[(2S,3S,4R,5R,6R)-4-{[(2S,3R,4S,5S)-5-{[(2R,3S,4R,5R,6R)-3-{[(2S,3S,4S,5R,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-{[(2R,3R,4S,5S,6S)-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. Versicoside A is found in Anasterias antarctica and Anasterias minuta. Based on a literature review very few articles have been published on [(2R,5S,7R,8R,10R,11R,14R,15R)-8-{[(2S,3S,4R,5R,6R)-4-{[(2S,3R,4S,5S)-5-{[(2R,3S,4R,5R,6R)-3-{[(2S,3S,4S,5R,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-{[(2R,3R,4S,5S,6S)-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]7O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]7O)[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/C62H102O33S/c1-22(2)15-26(65)18-62(8,79)36-10-9-29-28-17-32(31-16-27(95-96(80,81)82)11-13-60(31,6)30(28)12-14-61(29,36)7)87-56-48(77)51(39(68)24(4)85-56)92-58-52(93-54-46(75)43(72)37(66)23(3)84-54)42(71)35(21-83-58)90-59-53(45(74)41(70)34(20-64)89-59)94-57-49(78)50(38(67)25(5)86-57)91-55-47(76)44(73)40(69)33(19-63)88-55/h12,22-25,27-29,31-59,63-64,66-79H,9-11,13-21H2,1-8H3,(H,80,81,82)/t23-,24+,25-,27-,28+,29+,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+,57-,58-,59+,60-,61+,62+/m0/s1 |
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| Synonyms | | Value | Source |
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| [(2R,5S,7R,8R,10R,11R,14R,15R)-8-{[(2S,3S,4R,5R,6R)-4-{[(2S,3R,4S,5S)-5-{[(2R,3S,4R,5R,6R)-3-{[(2S,3S,4S,5R,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-{[(2R,3R,4S,5S,6S)-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,7R,8R,10R,11R,14R,15R)-8-{[(2S,3S,4R,5R,6R)-4-{[(2S,3R,4S,5S)-5-{[(2R,3S,4R,5R,6R)-3-{[(2S,3S,4S,5R,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-{[(2R,3R,4S,5S,6S)-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,7R,8R,10R,11R,14R,15R)-8-{[(2S,3S,4R,5R,6R)-4-{[(2S,3R,4S,5S)-5-{[(2R,3S,4R,5R,6R)-3-{[(2S,3S,4S,5R,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-{[(2R,3R,4S,5S,6S)-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 | C62H102O33S |
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| Average Mass | 1407.5300 Da |
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| Monoisotopic Mass | 1406.60241 Da |
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| IUPAC Name | [(2R,5S,7R,8R,10R,11R,14R,15R)-8-{[(2S,3S,4R,5R,6R)-4-{[(2S,3R,4S,5S)-5-{[(2R,3S,4R,5R,6R)-3-{[(2S,3S,4S,5R,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-{[(2R,3R,4S,5S,6S)-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,7R,8R,10R,11R,14R,15R)-8-{[(2S,3S,4R,5R,6R)-4-{[(2S,3R,4S,5S)-5-{[(2R,3S,4R,5R,6R)-3-{[(2S,3S,4S,5R,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-{[(2R,3R,4S,5S,6S)-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]7O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]7O)[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/C62H102O33S/c1-22(2)15-26(65)18-62(8,79)36-10-9-29-28-17-32(31-16-27(95-96(80,81)82)11-13-60(31,6)30(28)12-14-61(29,36)7)87-56-48(77)51(39(68)24(4)85-56)92-58-52(93-54-46(75)43(72)37(66)23(3)84-54)42(71)35(21-83-58)90-59-53(45(74)41(70)34(20-64)89-59)94-57-49(78)50(38(67)25(5)86-57)91-55-47(76)44(73)40(69)33(19-63)88-55/h12,22-25,27-29,31-59,63-64,66-79H,9-11,13-21H2,1-8H3,(H,80,81,82)/t23-,24+,25-,27-,28+,29+,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+,57-,58-,59+,60-,61+,62+/m0/s1 |
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| InChI Key | MQZKOPWRAJKFLS-GIGIEYMFSA-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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