| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-29 03:03:42 UTC |
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| Updated at | 2022-04-29 03:03:42 UTC |
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| NP-MRD ID | NP0082011 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (+)-Fuscaside A |
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| Description | [(1R,2S,5S,7S,8R,10S,11S,12S,14R,15R)-8,10-dihydroxy-2,15-dimethyl-14-[(2R,5S)-6-methyl-5-{[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-12-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. (+)-Fuscaside A is found in Lethasterias fusca. Based on a literature review very few articles have been published on [(1R,2S,5S,7S,8R,10S,11S,12S,14R,15R)-8,10-dihydroxy-2,15-dimethyl-14-[(2R,5S)-6-methyl-5-{[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-12-yl]oxidanesulfonic acid. |
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| Structure | CC(C)[C@H](CC[C@@H](C)[C@H]1C[C@H](OS(O)(=O)=O)[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H](C[C@@H]3[C@H](O)C[C@@]21O)O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O)O[C@@H]1OC[C@H](O)[C@H](O)[C@@H]1O InChI=1S/C37H64O16S/c1-17(2)25(52-34-31(44)29(42)24(40)16-50-34)7-6-18(3)20-13-26(53-54(46,47)48)32-36(20,5)11-9-27-35(4)10-8-19(12-21(35)22(38)14-37(27,32)45)51-33-30(43)28(41)23(39)15-49-33/h17-34,38-45H,6-16H2,1-5H3,(H,46,47,48)/t18-,19+,20-,21-,22-,23-,24+,25+,26+,27-,28+,29+,30-,31+,32-,33+,34+,35+,36-,37+/m1/s1 |
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| Synonyms | | Value | Source |
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| [(1R,2S,5S,7S,8R,10S,11S,12S,14R,15R)-8,10-Dihydroxy-2,15-dimethyl-14-[(2R,5S)-6-methyl-5-{[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}tetracyclo[8.7.0.0,.0,]heptadecan-12-yl]oxidanesulfonate | Generator | | [(1R,2S,5S,7S,8R,10S,11S,12S,14R,15R)-8,10-Dihydroxy-2,15-dimethyl-14-[(2R,5S)-6-methyl-5-{[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}tetracyclo[8.7.0.0,.0,]heptadecan-12-yl]oxidanesulphonate | Generator | | [(1R,2S,5S,7S,8R,10S,11S,12S,14R,15R)-8,10-Dihydroxy-2,15-dimethyl-14-[(2R,5S)-6-methyl-5-{[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}tetracyclo[8.7.0.0,.0,]heptadecan-12-yl]oxidanesulphonic acid | Generator |
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| Chemical Formula | C37H64O16S |
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| Average Mass | 796.9600 Da |
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| Monoisotopic Mass | 796.39151 Da |
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| IUPAC Name | [(1R,2S,5S,7S,8R,10S,11S,12S,14R,15R)-8,10-dihydroxy-2,15-dimethyl-14-[(2R,5S)-6-methyl-5-{[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-12-yl]oxidanesulfonic acid |
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| Traditional Name | [(1R,2S,5S,7S,8R,10S,11S,12S,14R,15R)-8,10-dihydroxy-2,15-dimethyl-14-[(2R,5S)-6-methyl-5-{[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}heptan-2-yl]-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-12-yl]oxidanesulfonic acid |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)[C@H](CC[C@@H](C)[C@H]1C[C@H](OS(O)(=O)=O)[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H](C[C@@H]3[C@H](O)C[C@@]21O)O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O)O[C@@H]1OC[C@H](O)[C@H](O)[C@@H]1O |
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| InChI Identifier | InChI=1S/C37H64O16S/c1-17(2)25(52-34-31(44)29(42)24(40)16-50-34)7-6-18(3)20-13-26(53-54(46,47)48)32-36(20,5)11-9-27-35(4)10-8-19(12-21(35)22(38)14-37(27,32)45)51-33-30(43)28(41)23(39)15-49-33/h17-34,38-45H,6-16H2,1-5H3,(H,46,47,48)/t18-,19+,20-,21-,22-,23-,24+,25+,26+,27-,28+,29+,30-,31+,32-,33+,34+,35+,36-,37+/m1/s1 |
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| InChI Key | BQMZNIWFFKRTDK-ASACJZMRSA-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 | | Species Name | Source | Reference |
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| Lethasterias fusca | Animalia | |
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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 | - Steroidal glycoside
- Monohydroxy bile acid, alcohol, or derivatives
- Hydroxy bile acid, alcohol, or derivatives
- Bile acid, alcohol, or derivatives
- Sulfated steroid skeleton
- Hydroxysteroid
- 6-hydroxysteroid
- O-glycosyl compound
- Glycosyl compound
- Sulfuric acid ester
- Alkyl sulfate
- Sulfate-ester
- Sulfuric acid monoester
- Oxane
- Monosaccharide
- Tertiary alcohol
- Organic sulfuric acid or derivatives
- Cyclic alcohol
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Acetal
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- 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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