Record Information |
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Version | 2.0 |
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Created at | 2021-06-20 22:45:16 UTC |
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Updated at | 2021-06-30 00:14:40 UTC |
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NP-MRD ID | NP0040648 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | totarol |
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Provided By | JEOL Database |
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Description | totarol is found in Afrocarpus gracilior, Apis mellifera, Biota orientalis, Callitropsis nootkatensis, Chamaecyparis formosensis, Chamaecyparis pisifera, Cryptomeria japonica, Cupressus sempervirens, Dacrycarpus vieillardii, Juniperus chinensis, Juniperus communis, Juniperus formosana, Juniperus phoenicea, Juniperus rigida, Nageia nagi, Platycladus orientalis, Podocarpus gnidioides, Podocarpus macrophyllus , Podocarpus sylvestris, Podocarpus totara, Podocarpus totara L. , Retrophyllum comptonii, Retrophyllum minus, Schistochila acuminata, Tetraclinis articulata, Thuja occidentalis, Thuja plicata, Thuja standishii and Thujopsis dolabrata. totarol was first documented in 2021 (PMID: 34227213). Based on a literature review a small amount of articles have been published on (+)-totarol (PMID: 33568294) (PMID: 34299601) (PMID: 34298240) (PMID: 34077024). |
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Structure | [H]OC1=C([H])C([H])=C2C(=C1C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] InChI=1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17-,20+/m0/s1 |
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Synonyms | Value | Source |
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4b,5,6,7,8,8a,9,10-Octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-2-phenanthrenol | MeSH | 14-Isopropylpodocarpa-8,11,13-trien-13-ol | MeSH |
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Chemical Formula | C20H30O |
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Average Mass | 286.4590 Da |
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Monoisotopic Mass | 286.22967 Da |
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IUPAC Name | (4bS,8aS)-4b,8,8-trimethyl-1-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-ol |
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Traditional Name | totarol |
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CAS Registry Number | Not Available |
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SMILES | [H]OC1=C([H])C([H])=C2C(=C1C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17-,20+/m0/s1 |
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InChI Key | ZRVDANDJSTYELM-FXAWDEMLSA-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, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
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Predicted Spectra |
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| Not Available |
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Chemical Shift Submissions |
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| Not Available |
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Species |
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Species of Origin | | Show more...
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Chemical Taxonomy |
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Classification | Not classified |
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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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External Links |
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HMDB ID | Not Available |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 83757 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | Not Available |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Good Scents ID | Not Available |
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References |
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General References | - Ribeiro VP, Arruda C, Aldana-Mejia JA, Bastos JK, Tripathi SK, Khan SI, Khan IA, Ali Z: Phytochemical, Antiplasmodial, Cytotoxic and Antimicrobial Evaluation of a Southeast Brazilian Brown Propolis Produced by Apis mellifera Bees. Chem Biodivers. 2021 Jul 5. doi: 10.1002/cbdv.202100288. [PubMed:34227213 ]
- Ma LT, Wang CH, Hon CY, Lee YR, Chu FH: Discovery and characterization of diterpene synthases in Chamaecyparis formosensis Matsum. which participated in an unprecedented diterpenoid biosynthesis route in conifer. Plant Sci. 2021 Mar;304:110790. doi: 10.1016/j.plantsci.2020.110790. Epub 2020 Dec 9. [PubMed:33568294 ]
- Kim C, Le D, Lee M: Diterpenoids Isolated from Podocarpus macrophyllus Inhibited the Inflammatory Mediators in LPS-Induced HT-29 and RAW 264.7 Cells. Molecules. 2021 Jul 17;26(14). pii: molecules26144326. doi: 10.3390/molecules26144326. [PubMed:34299601 ]
- Laamari Y, Oubella A, Bimoussa A, El Mansouri AE, Ketatni EM, Mentre O, Ait Itto MY, Morjani H, Khouili M, Auhmani A: Design, Hemiysnthesis, crystal structure and anticancer activity of 1, 2, 3-triazoles derivatives of totarol. Bioorg Chem. 2021 Oct;115:105165. doi: 10.1016/j.bioorg.2021.105165. Epub 2021 Jul 14. [PubMed:34298240 ]
- Xu T, Huang L, Liu Z, Ma D, Zhang G, Ning X, Lu X, Liu H, Jiang B: Totarol, a natural diterpenoid, induces selective antitumor activity in SGC-7901 human gastric carcinoma cells by triggering apoptosis, cell cycle disruption and suppression of cancer cell migration. J BUON. 2021 Mar-Apr;26(2):640. [PubMed:34077024 ]
- Zaugg, J., et al. (2011). Zaugg, J., et al, J. Nat. Prod. 74, 1764 (2011). J. Nat. Prod..
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