Record Information |
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Version | 1.0 |
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Created at | 2022-06-29 19:22:25 UTC |
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Updated at | 2022-06-29 19:22:25 UTC |
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NP-MRD ID | NP0138902 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Lannaconitine |
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Description | Lappaconitine belongs to the class of organic compounds known as lappaconitine-type diterpenoid alkaloids. These are c18-bisnorditerpenoid alkaloids with a structure based on the heptacyclic lappaconitine skeleton. Lappaconitine similar to aconitane, with the difference that the former lacks a carbon atom at the 18-position. It was first documented in 2022 (PMID: 35739330). Based on a literature review a significant number of articles have been published on lappaconitine (PMID: 35469829) (PMID: 35620295) (PMID: 35643327) (PMID: 35556222). |
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Structure | CCN1C[C@@]2(CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OC)[C@]5(O)[C@](O)(C[C@@H]6OC)[C@H](C[C@H]23)C14)OC(=O)C1=CC=CC=C1NC(C)=O InChI=1S/C32H44N2O8/c1-6-34-16-29(42-28(36)18-9-7-8-10-21(18)33-17(2)35)12-11-25(40-4)31-23(29)14-20(26(31)34)30(37)15-22(39-3)19-13-24(31)32(30,38)27(19)41-5/h7-10,19-20,22-27,37-38H,6,11-16H2,1-5H3,(H,33,35)/t19-,20-,22+,23-,24+,25+,26?,27+,29-,30+,31+,32+/m1/s1 |
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Synonyms | Value | Source |
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Lappacontine | MeSH |
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Chemical Formula | C32H44N2O8 |
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Average Mass | 584.7100 Da |
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Monoisotopic Mass | 584.30977 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 32854-75-4 |
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SMILES | CCN1C[C@@]2(CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OC)[C@]5(O)[C@](O)(C[C@@H]6OC)[C@H](C[C@H]23)C14)OC(=O)C1=CC=CC=C1NC(C)=O |
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InChI Identifier | InChI=1S/C32H44N2O8/c1-6-34-16-29(42-28(36)18-9-7-8-10-21(18)33-17(2)35)12-11-25(40-4)31-23(29)14-20(26(31)34)30(37)15-22(39-3)19-13-24(31)32(30,38)27(19)41-5/h7-10,19-20,22-27,37-38H,6,11-16H2,1-5H3,(H,33,35)/t19-,20-,22+,23-,24+,25+,26?,27+,29-,30+,31+,32+/m1/s1 |
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InChI Key | NWBWCXBPKTTZNQ-MUVXNFNYSA-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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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 | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as lappaconitine-type diterpenoid alkaloids. These are c18-bisnorditerpenoid alkaloids with a structure based on the heptacyclic lappaconitine skeleton. Lappaconitine similar to aconitane, with the difference that the former lacks a carbon atom at the 18-position. |
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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 | Lappaconitine-type diterpenoid alkaloids |
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Alternative Parents | |
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Substituents | - Lappaconitine-type diterpenoid alkaloid
- Acylaminobenzoic acid or derivatives
- Acetanilide
- Benzoate ester
- Quinolidine
- Benzoic acid or derivatives
- N-acetylarylamine
- Alkaloid or derivatives
- Anilide
- Benzoyl
- N-arylamide
- Azepane
- Monocyclic benzene moiety
- Piperidine
- Benzenoid
- Vinylogous amide
- Acetamide
- Cyclic alcohol
- Tertiary alcohol
- Amino acid or derivatives
- 1,2-diol
- Carboxamide group
- Carboxylic acid ester
- Tertiary aliphatic amine
- Secondary carboxylic acid amide
- Tertiary amine
- Dialkyl ether
- Monocarboxylic acid or derivatives
- Ether
- Carboxylic acid derivative
- Azacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Amine
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- 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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General References | - Zhang L, Miao X, Li Y, Hu F, Ma D, Zhang Z, Sun Q, Zhu Y, Zhu Q: Traditional processing, uses, phytochemistry, pharmacology and toxicology of Aconitum sinomontanum Nakai: A comprehensive review. J Ethnopharmacol. 2022 Jul 15;293:115317. doi: 10.1016/j.jep.2022.115317. Epub 2022 Apr 22. [PubMed:35469829 ]
- Jiang W, Tang M, Yang L, Zhao X, Gao J, Jiao Y, Li T, Tie C, Gao T, Han Y, Jiang JD: Analgesic Alkaloids Derived From Traditional Chinese Medicine in Pain Management. Front Pharmacol. 2022 May 10;13:851508. doi: 10.3389/fphar.2022.851508. eCollection 2022. [PubMed:35620295 ]
- Tsorin IB, Teplov IY, Zinchenko VP, Vititnova MB, Tsyrlina EM, Yunusov MS, Kryzhanovskii SA: Analysis of Electrophysiological Mechanisms of N-Deacetyllapaconitine Monochlorhydrate, the Main Metabolite of Lappaconitine Hydrobromide. Bull Exp Biol Med. 2022 Jun;173(2):219-223. doi: 10.1007/s10517-022-05522-2. Epub 2022 Jun 24. [PubMed:35739330 ]
- Chiu KM, Lin TY, Lee MY, Lu CW, Wang SJ: Lappaconitine inhibits glutamate release from rat cerebrocortical nerve terminals by suppressing Ca(2+) influx and protein kinase A cascade. Neurotoxicology. 2022 Jul;91:218-227. doi: 10.1016/j.neuro.2022.05.014. Epub 2022 May 25. [PubMed:35643327 ]
- McCabe DJ: Clinical Effects from Ingestion of Lappaconitine, an Aconitum Alkaloid with Sodium Channel Blocking Effects. J Med Toxicol. 2022 Jul;18(3):243-247. doi: 10.1007/s13181-022-00896-1. Epub 2022 May 13. [PubMed:35556222 ]
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