Record Information |
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Version | 1.0 |
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Created at | 2021-06-19 23:56:41 UTC |
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Updated at | 2021-06-30 00:03:07 UTC |
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NP-MRD ID | NP0033382 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 3,23-disulfate ester of 2alpha,3beta,19alpha,23-tetrahydroxyurs-12-en-28+ |
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Provided By | JEOL Database |
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Description | (1R,2R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-1,11-dihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-(sulfooxy)-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3,23-disulfate ester of 2alpha,3beta,19alpha,23-tetrahydroxyurs-12-en-28+ is found in Melissa officinalis and Melissa officinalis. It was first documented in 2002 (PMID: 33651529). Based on a literature review a significant number of articles have been published on (1R,2R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-1,11-dihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-(sulfooxy)-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454). |
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Structure | [H]OC(=O)[C@]12C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@](O[H])(C([H])([H])[H])[C@@]1([H])C1=C([H])C([H])([H])[C@]3([H])[C@@]4(C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@]([H])(O[S](=O)(=O)O[H])[C@@](C([H])([H])[H])(C([H])([H])O[S](=O)(=O)O[H])[C@]4([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]1(C([H])([H])[H])C([H])([H])C2([H])[H] InChI=1S/C30H48O12S2/c1-17-9-12-30(24(32)33)14-13-27(4)18(22(30)29(17,6)34)7-8-21-25(2)15-19(31)23(42-44(38,39)40)26(3,16-41-43(35,36)37)20(25)10-11-28(21,27)5/h7,17,19-23,31,34H,8-16H2,1-6H3,(H,32,33)(H,35,36,37)(H,38,39,40)/t17-,19-,20-,21-,22-,23+,25+,26+,27-,28-,29-,30+/m1/s1 |
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Synonyms | Value | Source |
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(1R,2R,4AS,6as,6BR,8ar,9R,10R,11R,12ar,12BR,14BS)-1,11-dihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-(sulfooxy)-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate | Generator | (1R,2R,4AS,6as,6BR,8ar,9R,10R,11R,12ar,12BR,14BS)-1,11-dihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-(sulphooxy)-9-[(sulphooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate | Generator | (1R,2R,4AS,6as,6BR,8ar,9R,10R,11R,12ar,12BR,14BS)-1,11-dihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-(sulphooxy)-9-[(sulphooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid | Generator |
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Chemical Formula | C30H48O12S2 |
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Average Mass | 664.8200 Da |
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Monoisotopic Mass | 664.25872 Da |
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IUPAC Name | (1R,2R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-1,11-dihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-(sulfooxy)-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid |
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Traditional Name | (1R,2R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-1,11-dihydroxy-1,2,6a,6b,9,12a-hexamethyl-10-(sulfooxy)-9-[(sulfooxy)methyl]-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]OC(=O)[C@]12C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@](O[H])(C([H])([H])[H])[C@@]1([H])C1=C([H])C([H])([H])[C@]3([H])[C@@]4(C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@]([H])(O[S](=O)(=O)O[H])[C@@](C([H])([H])[H])(C([H])([H])O[S](=O)(=O)O[H])[C@]4([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]1(C([H])([H])[H])C([H])([H])C2([H])[H] |
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InChI Identifier | InChI=1S/C30H48O12S2/c1-17-9-12-30(24(32)33)14-13-27(4)18(22(30)29(17,6)34)7-8-21-25(2)15-19(31)23(42-44(38,39)40)26(3,16-41-43(35,36)37)20(25)10-11-28(21,27)5/h7,17,19-23,31,34H,8-16H2,1-6H3,(H,32,33)(H,35,36,37)(H,38,39,40)/t17-,19-,20-,21-,22-,23+,25+,26+,27-,28-,29-,30+/m1/s1 |
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InChI Key | IYDFTWZTXDDZLY-NIZSJLHKSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CD3OD, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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 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
- Sulfated steroid skeleton
- 12-hydroxysteroid
- Hydroxysteroid
- 12-beta-hydroxysteroid
- Steroid
- Sulfuric acid ester
- Alkyl sulfate
- Sulfate-ester
- Sulfuric acid monoester
- Tertiary alcohol
- Cyclic alcohol
- Organic sulfuric acid or derivatives
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic 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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