| Record Information |
|---|
| Version | 2.0 |
|---|
| Created at | 2022-04-28 08:47:20 UTC |
|---|
| Updated at | 2022-04-28 08:47:20 UTC |
|---|
| NP-MRD ID | NP0064589 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | 3,11-Diacetoxy-2-bromo-beta-chamigrene |
|---|
| Description | (2R,3S,6S,11R)-11-(acetyloxy)-2-bromo-1,1,9-trimethyl-5-methylidenespiro[5.5]Undec-8-en-3-yl acetate belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae. 3,11-Diacetoxy-2-bromo-beta-chamigrene is found in Laurencia obtusa . Based on a literature review very few articles have been published on (2R,3S,6S,11R)-11-(acetyloxy)-2-bromo-1,1,9-trimethyl-5-methylidenespiro[5.5]Undec-8-en-3-yl acetate. |
|---|
| Structure | CC(=O)O[C@H]1CC(=C)[C@@]2(CC=C(C)C[C@H]2OC(C)=O)C(C)(C)[C@H]1Br InChI=1S/C19H27BrO4/c1-11-7-8-19(16(9-11)24-14(4)22)12(2)10-15(23-13(3)21)17(20)18(19,5)6/h7,15-17H,2,8-10H2,1,3-6H3/t15-,16+,17-,19+/m0/s1 |
|---|
| Synonyms | | Value | Source |
|---|
| (2R,3S,6S,11R)-11-(Acetyloxy)-2-bromo-1,1,9-trimethyl-5-methylidenespiro[5.5]undec-8-en-3-yl acetic acid | Generator |
|
|---|
| Chemical Formula | C19H27BrO4 |
|---|
| Average Mass | 399.3250 Da |
|---|
| Monoisotopic Mass | 398.10927 Da |
|---|
| IUPAC Name | (1R,6S,8R,9S)-9-(acetyloxy)-8-bromo-3,7,7-trimethyl-11-methylidenespiro[5.5]undec-3-en-1-yl acetate |
|---|
| Traditional Name | (1R,6S,8R,9S)-9-(acetyloxy)-8-bromo-3,7,7-trimethyl-11-methylidenespiro[5.5]undec-3-en-1-yl acetate |
|---|
| CAS Registry Number | Not Available |
|---|
| SMILES | CC(=O)O[C@H]1CC(=C)[C@@]2(CC=C(C)C[C@H]2OC(C)=O)C(C)(C)[C@H]1Br |
|---|
| InChI Identifier | InChI=1S/C19H27BrO4/c1-11-7-8-19(16(9-11)24-14(4)22)12(2)10-15(23-13(3)21)17(20)18(19,5)6/h7,15-17H,2,8-10H2,1,3-6H3/t15-,16+,17-,19+/m0/s1 |
|---|
| InChI Key | UFKFDTHMWZFEOE-MJQMVNBJSA-N |
|---|
| Experimental Spectra |
|---|
|
| Not Available | | Predicted Spectra |
|---|
|
| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
|---|
| 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 |
|---|
|
| Not Available | | Species |
|---|
| Species of Origin | |
|---|
| Chemical Taxonomy |
|---|
| Description | Belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Prenol lipids |
|---|
| Sub Class | Sesquiterpenoids |
|---|
| Direct Parent | Chamigranes |
|---|
| Alternative Parents | |
|---|
| Substituents | - Chamigrane sesquiterpenoid
- Dicarboxylic acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organobromide
- Organohalogen compound
- Carbonyl group
- Alkyl halide
- Alkyl bromide
- Aliphatic homopolycyclic compound
|
|---|
| Molecular Framework | Aliphatic homopolycyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Physical Properties |
|---|
| State | Not Available |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|