| Record Information |
|---|
| Version | 2.0 |
|---|
| Created at | 2022-04-28 10:18:37 UTC |
|---|
| Updated at | 2022-04-28 10:18:37 UTC |
|---|
| NP-MRD ID | NP0066144 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | Tafricanin A |
|---|
| Description | [(1R,2R,4aS,5S,5'S,8aS)-5-(chloromethyl)-5'-(furan-3-yl)-5-hydroxy-2-methyl-2',4,6-trioxo-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-4a-yl]methyl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Tafricanin A is found in Teucrium africanum and Teucrium pestalozzae. Based on a literature review very few articles have been published on [(1R,2R,4aS,5S,5'S,8aS)-5-(chloromethyl)-5'-(furan-3-yl)-5-hydroxy-2-methyl-2',4,6-trioxo-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-4a-yl]methyl acetate. |
|---|
| Structure | C[C@@H]1CC(=O)[C@]2(COC(C)=O)[C@H](CCC(=O)[C@]2(O)CCl)[C@@]11C[C@H](OC1=O)C1=COC=C1 InChI=1S/C22H25ClO8/c1-12-7-18(26)21(11-30-13(2)24)16(3-4-17(25)22(21,28)10-23)20(12)8-15(31-19(20)27)14-5-6-29-9-14/h5-6,9,12,15-16,28H,3-4,7-8,10-11H2,1-2H3/t12-,15+,16-,20-,21+,22-/m1/s1 |
|---|
| Synonyms | | Value | Source |
|---|
| [(1R,2R,4AS,5S,5's,8as)-5-(chloromethyl)-5'-(furan-3-yl)-5-hydroxy-2-methyl-2',4,6-trioxo-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-4a-yl]methyl acetic acid | Generator |
|
|---|
| Chemical Formula | C22H25ClO8 |
|---|
| Average Mass | 452.8800 Da |
|---|
| Monoisotopic Mass | 452.12380 Da |
|---|
| IUPAC Name | [(1R,2R,4aS,5S,5'S,8aS)-5-(chloromethyl)-5'-(furan-3-yl)-5-hydroxy-2-methyl-2',4,6-trioxo-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-4a-yl]methyl acetate |
|---|
| Traditional Name | (1R,2R,4aS,5S,5'S,8aS)-5-(chloromethyl)-5'-(furan-3-yl)-5-hydroxy-2-methyl-2',4,6-trioxo-tetrahydro-2H-spiro[naphthalene-1,3'-oxolane]-4a-ylmethyl acetate |
|---|
| CAS Registry Number | Not Available |
|---|
| SMILES | C[C@@H]1CC(=O)[C@]2(COC(C)=O)[C@H](CCC(=O)[C@]2(O)CCl)[C@@]11C[C@H](OC1=O)C1=COC=C1 |
|---|
| InChI Identifier | InChI=1S/C22H25ClO8/c1-12-7-18(26)21(11-30-13(2)24)16(3-4-17(25)22(21,28)10-23)20(12)8-15(31-19(20)27)14-5-6-29-9-14/h5-6,9,12,15-16,28H,3-4,7-8,10-11H2,1-2H3/t12-,15+,16-,20-,21+,22-/m1/s1 |
|---|
| InChI Key | JPVQRCXHVVLUCP-LCJNUFCQSA-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 diterpene lactones. These are diterpenoids containing a lactone moiety. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Prenol lipids |
|---|
| Sub Class | Terpene lactones |
|---|
| Direct Parent | Diterpene lactones |
|---|
| Alternative Parents | |
|---|
| Substituents | - Diterpene lactone
- Diterpenoid
- Clerodane diterpenoid
- Acyloin
- Dicarboxylic acid or derivatives
- Gamma butyrolactone
- Cyclic alcohol
- Heteroaromatic compound
- Furan
- Tetrahydrofuran
- Tertiary alcohol
- Carboxylic acid ester
- Chlorohydrin
- Cyclic ketone
- Halohydrin
- Ketone
- Lactone
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Alkyl chloride
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organic oxygen compound
- Organooxygen compound
- Alkyl halide
- Carbonyl group
- Organohalogen compound
- Organochloride
- Aromatic heteropolycyclic compound
|
|---|
| Molecular Framework | Aromatic heteropolycyclic 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 | |
|---|