| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 16:46:37 UTC |
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| Updated at | 2022-04-28 16:46:37 UTC |
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| NP-MRD ID | NP0071394 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (+)-Karavilagenin A 3-glucoside |
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| Description | (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1S,2S,5S,9R,10R,11S,14R,15R)-9-methoxy-14-[(2R,4E)-6-methoxy-6-methylhept-4-en-2-yl]-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}oxane-3,4,5-triol 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. (+)-Karavilagenin A 3-glucoside is found in Momordica charantia L. . Based on a literature review very few articles have been published on (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1S,2S,5S,9R,10R,11S,14R,15R)-9-methoxy-14-[(2R,4E)-6-methoxy-6-methylhept-4-en-2-yl]-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}oxane-3,4,5-triol. |
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| Structure | CO[C@@H]1C=C2[C@@H](CC[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C2(C)C)[C@]2(C)CC[C@]3(C)[C@H](CC[C@@]3(C)[C@H]12)[C@H](C)C\C=C\C(C)(C)OC InChI=1S/C38H64O8/c1-22(12-11-16-34(2,3)44-10)23-15-17-38(8)32-26(43-9)20-25-24(36(32,6)18-19-37(23,38)7)13-14-28(35(25,4)5)46-33-31(42)30(41)29(40)27(21-39)45-33/h11,16,20,22-24,26-33,39-42H,12-15,17-19,21H2,1-10H3/b16-11+/t22-,23-,24-,26-,27-,28+,29-,30+,31-,32-,33+,36+,37-,38+/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C38H64O8 |
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| Average Mass | 648.9220 Da |
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| Monoisotopic Mass | 648.46012 Da |
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| IUPAC Name | (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1S,2S,5S,9R,10R,11S,14R,15R)-9-methoxy-14-[(2R,4E)-6-methoxy-6-methylhept-4-en-2-yl]-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}oxane-3,4,5-triol |
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| Traditional Name | (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1S,2S,5S,9R,10R,11S,14R,15R)-9-methoxy-14-[(2R,4E)-6-methoxy-6-methylhept-4-en-2-yl]-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}oxane-3,4,5-triol |
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| CAS Registry Number | Not Available |
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| SMILES | CO[C@@H]1C=C2[C@@H](CC[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C2(C)C)[C@]2(C)CC[C@]3(C)[C@H](CC[C@@]3(C)[C@H]12)[C@H](C)C\C=C\C(C)(C)OC |
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| InChI Identifier | InChI=1S/C38H64O8/c1-22(12-11-16-34(2,3)44-10)23-15-17-38(8)32-26(43-9)20-25-24(36(32,6)18-19-37(23,38)7)13-14-28(35(25,4)5)46-33-31(42)30(41)29(40)27(21-39)45-33/h11,16,20,22-24,26-33,39-42H,12-15,17-19,21H2,1-10H3/b16-11+/t22-,23-,24-,26-,27-,28+,29-,30+,31-,32-,33+,36+,37-,38+/m1/s1 |
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| InChI Key | YCUBHAWXGLKZIA-WJCRZFIDSA-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
- Triterpenoid
- Cucurbitacin skeleton
- 14-alpha-methylsteroid
- Delta-5-steroid
- O-glycosyl compound
- Glycosyl compound
- Oxane
- Monosaccharide
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Ether
- Dialkyl ether
- Acetal
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- 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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