| Record Information |
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| Version | 2.0 |
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| Created at | 2022-06-29 19:59:09 UTC |
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| Updated at | 2022-06-29 19:59:09 UTC |
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| NP-MRD ID | NP0139541 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Tuberostemonine |
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| Description | Tuberostemonine belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively. Tuberostemonine is found in Stemona japonica, Stemona phyllantha, Stemona sessilifolia and Stemona tuberosa. Tuberostemonine was first documented in 2017 (PMID: 28580601). Based on a literature review a small amount of articles have been published on Tuberostemonine (PMID: 30225138) (PMID: 34731755) (PMID: 34212514). |
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| Structure | CC[C@H]1[C@@H]2OC(=O)[C@@H](C)[C@@H]2[C@H]2C[C@@H]([C@@H]3C[C@H](C)C(=O)O3)N3CCCC[C@H]1[C@H]23 InChI=1S/C22H33NO4/c1-4-13-14-7-5-6-8-23-16(17-9-11(2)21(24)26-17)10-15(19(14)23)18-12(3)22(25)27-20(13)18/h11-20H,4-10H2,1-3H3/t11-,12-,13+,14+,15+,16-,17-,18+,19+,20-/m0/s1 |
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| Synonyms | | Value | Source |
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| Tubero-stemonine | MeSH |
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| Chemical Formula | C22H33NO4 |
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| Average Mass | 375.5090 Da |
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| Monoisotopic Mass | 375.24096 Da |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | Not Available |
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| SMILES | CC[C@H]1[C@@H]2OC(=O)[C@@H](C)[C@@H]2[C@H]2C[C@@H]([C@@H]3C[C@H](C)C(=O)O3)N3CCCC[C@H]1[C@H]23 |
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| InChI Identifier | InChI=1S/C22H33NO4/c1-4-13-14-7-5-6-8-23-16(17-9-11(2)21(24)26-17)10-15(19(14)23)18-12(3)22(25)27-20(13)18/h11-20H,4-10H2,1-3H3/t11-,12-,13+,14+,15+,16-,17-,18+,19+,20-/m0/s1 |
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| InChI Key | GYOGHROCTSEKDY-JJDZUBOLSA-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 | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Stemona alkaloids |
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| Sub Class | Stemoamide-type alkaloids |
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| Direct Parent | Stichoneurine-type alkaloids |
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| Alternative Parents | |
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| Substituents | - Stichoneurine-type alkaloid
- Stenine backbone
- Indole or derivatives
- Azepane
- Dicarboxylic acid or derivatives
- Gamma butyrolactone
- N-alkylpyrrolidine
- Pyrrolidine
- Tetrahydrofuran
- Amino acid or derivatives
- Carboxylic acid ester
- Lactone
- Tertiary amine
- Tertiary aliphatic amine
- Carboxylic acid derivative
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Organic nitrogen compound
- Carbonyl group
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | |
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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 | - Pudjiastuti P, Puspaningsih NNT, Siswanto I, Fanani MZ, Ariga YK, Hase T, Sarker SD, Nahar L: Inhibitory Activity and Docking Analysis of Antimalarial Agents from Stemona sp. toward Ferredoxin-NADP+ Reductase from Malaria Parasites. J Parasitol Res. 2018 Aug 26;2018:3469132. doi: 10.1155/2018/3469132. eCollection 2018. [PubMed:30225138 ]
- Chen G, Brecker L, Felsinger S, Cai XH, Kongkiatpaiboon S, Schinnerl J: Morphological and chemical variation of Stemona tuberosa from southern China - Evidence for heterogeneity of this medicinal plant species. Plant Biol (Stuttg). 2017 Sep;19(5):835-842. doi: 10.1111/plb.12587. Epub 2017 Jun 28. [PubMed:28580601 ]
- Zheng X, Fan H, Song Z, Cheng P, Jiang H, Shi W, Xiao C, Wang J, Li Q, Yin G, Zhao X: Immobilized beta(2)-adrenergic receptor: A powerful chromatographic platform for drug discovery and evaluation of drug-like property for natural products. J Chromatogr A. 2021 Dec 6;1659:462635. doi: 10.1016/j.chroma.2021.462635. Epub 2021 Oct 21. [PubMed:34731755 ]
- Fu X, Zhao X, Zheng X, Wang T, Shayiranbieke A, Li L, Cao F, Ren J, Li Q, Zhao X: Rapidly identifying bioactive compounds from Zhisou oral liquid by immobilized receptor-based high-performance affinity chromatography. J Sep Sci. 2021 Sep;44(17):3219-3228. doi: 10.1002/jssc.202100174. Epub 2021 Jul 11. [PubMed:34212514 ]
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