Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 22:43:42 UTC |
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Updated at | 2022-04-28 22:43:42 UTC |
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NP-MRD ID | NP0077593 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (-)-Frondoside D |
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Description | [(3R,4R,5R,6S)-6-{[(2S,4S,5R,6S,9S,12S,13R,16S,18R)-4-(acetyloxy)-6-[(2S)-2-hydroxy-4-methylpentyl]-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]Icos-1(20)-en-16-yl]oxy}-5-{[(2S,3R,4S,5S,6R)-5-{[(2S,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-4-hydroxy-6-methyl-3-{[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxyoxan-3-yl]oxidanesulfonic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (-)-Frondoside D is found in Cucumaria frondosa. Based on a literature review very few articles have been published on [(3R,4R,5R,6S)-6-{[(2S,4S,5R,6S,9S,12S,13R,16S,18R)-4-(acetyloxy)-6-[(2S)-2-hydroxy-4-methylpentyl]-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]Icos-1(20)-en-16-yl]oxy}-5-{[(2S,3R,4S,5S,6R)-5-{[(2S,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-4-hydroxy-6-methyl-3-{[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxyoxan-3-yl]oxidanesulfonic acid. |
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Structure | CO[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)CO[C@@H](O[C@@H]3[C@@H](C)O[C@@H](O[C@@H]4[C@@H](O)[C@@H](CO[C@H]4O[C@H]4CC[C@]5(C)[C@@H]6CC[C@]78[C@H]([C@H](C[C@@]7(C)C6=CC[C@H]5C4(C)C)OC(C)=O)[C@](C)(C[C@@H](O)CC(C)C)OC8=O)OS(O)(=O)=O)[C@H](O[C@H]4OC[C@H](O)[C@H](O)[C@@H]4O)[C@H]3O)[C@@H]2O)[C@@H]1O InChI=1S/C60H96O30S/c1-24(2)17-27(63)18-59(9)49-32(82-26(4)62)19-58(8)29-11-12-35-56(5,6)36(14-15-57(35,7)28(29)13-16-60(49,58)55(73)89-59)84-53-47(39(68)34(23-80-53)90-91(74,75)76)88-54-48(87-50-40(69)37(66)30(64)21-78-50)41(70)44(25(3)81-54)85-51-42(71)45(31(65)22-79-51)86-52-43(72)46(77-10)38(67)33(20-61)83-52/h11,24-25,27-28,30-54,61,63-72H,12-23H2,1-10H3,(H,74,75,76)/t25-,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+,57-,58+,59+,60-/m1/s1 |
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Synonyms | Value | Source |
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[(3R,4R,5R,6S)-6-{[(2S,4S,5R,6S,9S,12S,13R,16S,18R)-4-(acetyloxy)-6-[(2S)-2-hydroxy-4-methylpentyl]-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0,.0,.0,]icos-1(20)-en-16-yl]oxy}-5-{[(2S,3R,4S,5S,6R)-5-{[(2S,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-4-hydroxy-6-methyl-3-{[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxyoxan-3-yl]oxidanesulfonate | Generator | [(3R,4R,5R,6S)-6-{[(2S,4S,5R,6S,9S,12S,13R,16S,18R)-4-(acetyloxy)-6-[(2S)-2-hydroxy-4-methylpentyl]-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0,.0,.0,]icos-1(20)-en-16-yl]oxy}-5-{[(2S,3R,4S,5S,6R)-5-{[(2S,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-4-hydroxy-6-methyl-3-{[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxyoxan-3-yl]oxidanesulphonate | Generator | [(3R,4R,5R,6S)-6-{[(2S,4S,5R,6S,9S,12S,13R,16S,18R)-4-(acetyloxy)-6-[(2S)-2-hydroxy-4-methylpentyl]-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0,.0,.0,]icos-1(20)-en-16-yl]oxy}-5-{[(2S,3R,4S,5S,6R)-5-{[(2S,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-4-hydroxy-6-methyl-3-{[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxyoxan-3-yl]oxidanesulphonic acid | Generator |
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Chemical Formula | C60H96O30S |
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Average Mass | 1329.4600 Da |
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Monoisotopic Mass | 1328.57071 Da |
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IUPAC Name | [(3R,4R,5R,6S)-6-{[(2S,4S,5R,6S,9S,12S,13R,16S,18R)-4-(acetyloxy)-6-[(2S)-2-hydroxy-4-methylpentyl]-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-1(20)-en-16-yl]oxy}-5-{[(2S,3R,4S,5S,6R)-5-{[(2S,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-4-hydroxy-6-methyl-3-{[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxyoxan-3-yl]oxidanesulfonic acid |
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Traditional Name | [(3R,4R,5R,6S)-6-{[(2S,4S,5R,6S,9S,12S,13R,16S,18R)-4-(acetyloxy)-6-[(2S)-2-hydroxy-4-methylpentyl]-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-1(20)-en-16-yl]oxy}-5-{[(2S,3R,4S,5S,6R)-5-{[(2S,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-4-hydroxy-6-methyl-3-{[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxyoxan-3-yl]oxidanesulfonic acid |
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CAS Registry Number | Not Available |
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SMILES | CO[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)CO[C@@H](O[C@@H]3[C@@H](C)O[C@@H](O[C@@H]4[C@@H](O)[C@@H](CO[C@H]4O[C@H]4CC[C@]5(C)[C@@H]6CC[C@]78[C@H]([C@H](C[C@@]7(C)C6=CC[C@H]5C4(C)C)OC(C)=O)[C@](C)(C[C@@H](O)CC(C)C)OC8=O)OS(O)(=O)=O)[C@H](O[C@H]4OC[C@H](O)[C@H](O)[C@@H]4O)[C@H]3O)[C@@H]2O)[C@@H]1O |
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InChI Identifier | InChI=1S/C60H96O30S/c1-24(2)17-27(63)18-59(9)49-32(82-26(4)62)19-58(8)29-11-12-35-56(5,6)36(14-15-57(35,7)28(29)13-16-60(49,58)55(73)89-59)84-53-47(39(68)34(23-80-53)90-91(74,75)76)88-54-48(87-50-40(69)37(66)30(64)21-78-50)41(70)44(25(3)81-54)85-51-42(71)45(31(65)22-79-51)86-52-43(72)46(77-10)38(67)33(20-61)83-52/h11,24-25,27-28,30-54,61,63-72H,12-23H2,1-10H3,(H,74,75,76)/t25-,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+,57-,58+,59+,60-/m1/s1 |
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InChI Key | OVYVNQVEMFBVCF-XZLICAFZSA-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 |
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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 triterpenoids. These are terpene molecules containing six isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Triterpenoids |
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Direct Parent | Triterpenoids |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Steroidal glycoside
- Oligosaccharide
- Monohydroxy bile acid, alcohol, or derivatives
- 23-hydroxysteroid
- Hydroxy bile acid, alcohol, or derivatives
- Bile acid, alcohol, or derivatives
- Steroid ester
- Hydroxysteroid
- Steroid
- O-glycosyl compound
- Glycosyl compound
- Sulfuric acid ester
- Alkyl sulfate
- Sulfate-ester
- Sulfuric acid monoester
- Oxane
- Gamma butyrolactone
- Dicarboxylic acid or derivatives
- Tetrahydrofuran
- Organic sulfuric acid or derivatives
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- 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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