Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 22:39:48 UTC |
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Updated at | 2022-04-28 22:39:48 UTC |
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NP-MRD ID | NP0077525 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (+)-Astraverrucin V |
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Description | (2R,3R,4S,5R,6R)-2-{[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9,14-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-yl]oxy}-3-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. (+)-Astraverrucin V is found in Astragalus verrucosus. Based on a literature review very few articles have been published on (2R,3R,4S,5R,6R)-2-{[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9,14-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-yl]oxy}-3-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl acetate. |
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Structure | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@H]3CC[C@]45C[C@]44CC[C@]6(C)[C@H]([C@@H](O)C[C@@]6(C)[C@@H]4C[C@H](O)[C@H]5C3(C)C)[C@@]3(C)CC[C@H](O3)C(C)(C)O)[C@H](O)[C@@H]2OC(C)=O)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C44H72O15/c1-20-28(49)29(50)30(51)36(54-20)58-32-24(18-45)56-37(31(52)33(32)55-21(2)46)57-26-11-13-44-19-43(44)15-14-40(7)35(42(9)12-10-27(59-42)39(5,6)53)23(48)17-41(40,8)25(43)16-22(47)34(44)38(26,3)4/h20,22-37,45,47-53H,10-19H2,1-9H3/t20-,22-,23-,24+,25-,26-,27-,28-,29+,30+,31+,32+,33-,34-,35-,36-,37-,40+,41-,42+,43-,44+/m0/s1 |
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Synonyms | Value | Source |
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(2R,3R,4S,5R,6R)-2-{[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9,14-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0,.0,.0,]octadecan-6-yl]oxy}-3-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl acetic acid | Generator |
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Chemical Formula | C44H72O15 |
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Average Mass | 841.0450 Da |
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Monoisotopic Mass | 840.48712 Da |
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IUPAC Name | (2R,3R,4S,5R,6R)-2-{[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9,14-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]oxy}-3-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl acetate |
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Traditional Name | (2R,3R,4S,5R,6R)-2-{[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9,14-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]oxy}-3-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@H]3CC[C@]45C[C@]44CC[C@]6(C)[C@H]([C@@H](O)C[C@@]6(C)[C@@H]4C[C@H](O)[C@H]5C3(C)C)[C@@]3(C)CC[C@H](O3)C(C)(C)O)[C@H](O)[C@@H]2OC(C)=O)[C@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C44H72O15/c1-20-28(49)29(50)30(51)36(54-20)58-32-24(18-45)56-37(31(52)33(32)55-21(2)46)57-26-11-13-44-19-43(44)15-14-40(7)35(42(9)12-10-27(59-42)39(5,6)53)23(48)17-41(40,8)25(43)16-22(47)34(44)38(26,3)4/h20,22-37,45,47-53H,10-19H2,1-9H3/t20-,22-,23-,24+,25-,26-,27-,28-,29+,30+,31+,32+,33-,34-,35-,36-,37-,40+,41-,42+,43-,44+/m0/s1 |
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InChI Key | LGKAGWLVEGCQQV-IKTFSFPJSA-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 cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. |
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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 | Cucurbitacin glycosides |
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Alternative Parents | |
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Substituents | - Cucurbitacin glycoside skeleton
- Triterpene saponin
- Triterpene glycoside
- Cycloartanol-skeleton
- Triterpenoid
- Cycloartane-skeleton
- 9b,19-cyclo-lanostane-skeleton
- 16-hydroxysteroid
- 16-beta-hydroxysteroid
- Hydroxysteroid
- 6-hydroxysteroid
- O-glycosyl compound
- Glycosyl compound
- Disaccharide
- Oxane
- Tetrahydrofuran
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Monocarboxylic acid or derivatives
- 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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