Record Information |
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Version | 2.0 |
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Created at | 2022-09-06 18:52:48 UTC |
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Updated at | 2022-09-06 18:52:48 UTC |
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NP-MRD ID | NP0236072 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,2r,3as,3bs,9ar,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-2-yl acetate |
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Description | (1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-13-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. (1r,2r,3as,3bs,9ar,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-2-yl acetate is found in Gratiola officinalis. Based on a literature review very few articles have been published on (1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-13-yl acetate. |
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Structure | CC(=O)O[C@@H]1C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]2(C)[C@H]1[C@@](C)(O)C(=O)\C=C\C(C)(C)O InChI=1S/C38H54O13/c1-18(40)49-22-15-35(6)24-11-10-19-20(14-21(31(46)34(19,4)5)50-32-29(45)28(44)27(43)23(17-39)51-32)37(24,8)26(42)16-36(35,7)30(22)38(9,48)25(41)12-13-33(2,3)47/h10,12-14,20,22-24,27-30,32,39,43-45,47-48H,11,15-17H2,1-9H3/b13-12+/t20-,22-,23-,24+,27-,28+,29-,30+,32-,35+,36-,37+,38+/m1/s1 |
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Synonyms | Value | Source |
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(1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-Dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0,.0,]heptadeca-3,7-dien-13-yl acetic acid | Generator |
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Chemical Formula | C38H54O13 |
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Average Mass | 718.8370 Da |
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Monoisotopic Mass | 718.35644 Da |
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IUPAC Name | (1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-13-yl acetate |
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Traditional Name | (1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-13-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)O[C@@H]1C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]2(C)[C@H]1[C@@](C)(O)C(=O)\C=C\C(C)(C)O |
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InChI Identifier | InChI=1S/C38H54O13/c1-18(40)49-22-15-35(6)24-11-10-19-20(14-21(31(46)34(19,4)5)50-32-29(45)28(44)27(43)23(17-39)51-32)37(24,8)26(42)16-36(35,7)30(22)38(9,48)25(41)12-13-33(2,3)47/h10,12-14,20,22-24,27-30,32,39,43-45,47-48H,11,15-17H2,1-9H3/b13-12+/t20-,22-,23-,24+,27-,28+,29-,30+,32-,35+,36-,37+,38+/m1/s1 |
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InChI Key | WVVGJLXJXQDKGS-KSWGJDELSA-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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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
- Cucurbitacin skeleton
- Triterpenoid
- 25-hydroxysteroid
- 22-oxosteroid
- 21-oxosteroid
- 20-hydroxysteroid
- Steroid ester
- 3-oxosteroid
- 3-oxo-delta-1-steroid
- Hydroxysteroid
- Oxosteroid
- 11-oxosteroid
- 14-alpha-methylsteroid
- Delta-1-steroid
- Hexose monosaccharide
- Glycosyl compound
- O-glycosyl compound
- Cyclohexenone
- Oxane
- Monosaccharide
- Acyloin
- Alpha,beta-unsaturated ketone
- Alpha-hydroxy ketone
- Acryloyl-group
- Enone
- Tertiary alcohol
- Carboxylic acid ester
- Ketone
- Cyclic ketone
- Secondary alcohol
- Polyol
- Carboxylic acid derivative
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Carbonyl group
- Alcohol
- Organic oxygen compound
- Organic oxide
- Primary alcohol
- Organooxygen compound
- 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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