| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 10:18:28 UTC |
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| Updated at | 2022-04-28 10:18:29 UTC |
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| NP-MRD ID | NP0066141 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Teuvincentin A |
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| Description | [(1S,2'R,4aS,5R,5'S,8aR)-2'-(acetyloxy)-5-(chloromethyl)-5'-(furan-3-yl)-3,5-dihydroxy-2-methyl-4-oxo-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,3'-oxolane]-4a-yl]methyl acetate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. Teuvincentin A is found in Teucrium polium . Based on a literature review very few articles have been published on [(1S,2'R,4aS,5R,5'S,8aR)-2'-(acetyloxy)-5-(chloromethyl)-5'-(furan-3-yl)-3,5-dihydroxy-2-methyl-4-oxo-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,3'-oxolane]-4a-yl]methyl acetate. |
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| Structure | CC(=O)OC[C@@]12[C@H](CCC[C@]1(O)CCl)[C@@]1(C[C@H](O[C@@H]1OC(C)=O)C1=COC=C1)C(C)=C(O)C2=O InChI=1S/C24H29ClO9/c1-13-19(28)20(29)24(12-32-14(2)26)18(5-4-7-22(24,30)11-25)23(13)9-17(16-6-8-31-10-16)34-21(23)33-15(3)27/h6,8,10,17-18,21,28,30H,4-5,7,9,11-12H2,1-3H3/t17-,18+,21-,22-,23+,24-/m0/s1 |
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| Synonyms | | Value | Source |
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| [(1S,2'r,4AS,5R,5's,8ar)-2'-(acetyloxy)-5-(chloromethyl)-5'-(furan-3-yl)-3,5-dihydroxy-2-methyl-4-oxo-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,3'-oxolane]-4a-yl]methyl acetic acid | Generator |
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| Chemical Formula | C24H29ClO9 |
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| Average Mass | 496.9400 Da |
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| Monoisotopic Mass | 496.15001 Da |
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| IUPAC Name | [(1S,2'R,4aS,5R,5'S,8aR)-2'-(acetyloxy)-5-(chloromethyl)-5'-(furan-3-yl)-3,5-dihydroxy-2-methyl-4-oxo-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,3'-oxolane]-4a-yl]methyl acetate |
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| Traditional Name | (1S,2'R,4aS,5R,5'S,8aR)-2'-(acetyloxy)-5-(chloromethyl)-5'-(furan-3-yl)-3,5-dihydroxy-2-methyl-4-oxo-6,7,8,8a-tetrahydrospiro[naphthalene-1,3'-oxolane]-4a-ylmethyl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | CC(=O)OC[C@@]12[C@H](CCC[C@]1(O)CCl)[C@@]1(C[C@H](O[C@@H]1OC(C)=O)C1=COC=C1)C(C)=C(O)C2=O |
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| InChI Identifier | InChI=1S/C24H29ClO9/c1-13-19(28)20(29)24(12-32-14(2)26)18(5-4-7-22(24,30)11-25)23(13)9-17(16-6-8-31-10-16)34-21(23)33-15(3)27/h6,8,10,17-18,21,28,30H,4-5,7,9,11-12H2,1-3H3/t17-,18+,21-,22-,23+,24-/m0/s1 |
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| InChI Key | KPNUSXYEBKSOIF-QJTPNWFNSA-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 colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. |
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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 | Diterpenoids |
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| Direct Parent | Colensane and clerodane diterpenoids |
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| Alternative Parents | |
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| Substituents | - Clerodane diterpenoid
- Cyclohexenone
- Dicarboxylic acid or derivatives
- Heteroaromatic compound
- Tetrahydrofuran
- Tertiary alcohol
- Furan
- Cyclic alcohol
- Ketone
- Halohydrin
- Chlorohydrin
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Enol
- Carboxylic acid derivative
- Acetal
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organochloride
- Organohalogen compound
- Carbonyl group
- Alkyl halide
- Alkyl chloride
- Alcohol
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic 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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