| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-27 22:30:37 UTC |
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| Updated at | 2022-04-27 22:30:37 UTC |
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| NP-MRD ID | NP0051070 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Dendrobine |
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| Description | Dendrobine belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Dendrobine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Dendrobine is found in Dendrobium chrysanthum, Dendrobium linawianum and Dendrobium nobile . Dendrobine was first documented in 2021 (PMID: 35069479). Based on a literature review a small amount of articles have been published on Dendrobine (PMID: 35417048) (PMID: 35299950) (PMID: 35238089) (PMID: 34975823). |
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| Structure | CC(C)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@@H]1CC[C@@H]3CN(C)[C@H]2[C@]13C InChI=1S/C16H25NO2/c1-8(2)11-12-10-6-5-9-7-17(4)14(16(9,10)3)13(11)19-15(12)18/h8-14H,5-7H2,1-4H3/t9-,10+,11+,12-,13-,14-,16+/m1/s1 |
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| Synonyms | | Value | Source |
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| Dendrobine hydrochloride | MeSH |
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| Chemical Formula | C16H25NO2 |
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| Average Mass | 263.3810 Da |
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| Monoisotopic Mass | 263.18853 Da |
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| IUPAC Name | (1S,4S,7S,8R,11R,12R,13S)-2,12-dimethyl-13-(propan-2-yl)-10-oxa-2-azatetracyclo[5.4.1.1^{8,11}.0^{4,12}]tridecan-9-one |
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| Traditional Name | (1S,4S,7S,8R,11R,12R,13S)-13-isopropyl-2,12-dimethyl-10-oxa-2-azatetracyclo[5.4.1.1^{8,11}.0^{4,12}]tridecan-9-one |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@@H]1CC[C@@H]3CN(C)[C@H]2[C@]13C |
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| InChI Identifier | InChI=1S/C16H25NO2/c1-8(2)11-12-10-6-5-9-7-17(4)14(16(9,10)3)13(11)19-15(12)18/h8-14H,5-7H2,1-4H3/t9-,10+,11+,12-,13-,14-,16+/m1/s1 |
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| InChI Key | RYAHJFGVOCZDEI-UFFNCVEVSA-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 indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Indoles and derivatives |
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| Sub Class | Not Available |
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| Direct Parent | Indoles and derivatives |
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| Alternative Parents | |
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| Substituents | - Indole or derivatives
- Caprolactone
- Oxepane
- Gamma butyrolactone
- N-alkylpyrrolidine
- Pyrrolidine
- Tetrahydrofuran
- Amino acid or derivatives
- Carboxylic acid ester
- Lactone
- Tertiary amine
- Tertiary aliphatic amine
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Oxacycle
- Azacycle
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Hydrocarbon derivative
- 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 | - Lou D, Xing X, Liang Y: Dendrobine modulates autophagy to alleviate ox-LDL-induced oxidative stress and senescence in HUVECs. Drug Dev Res. 2022 Apr 13. doi: 10.1002/ddr.21937. [PubMed:35417048 ]
- Xu Q, Niu SC, Li KL, Zheng PJ, Zhang XJ, Jia Y, Liu Y, Niu YX, Yu LH, Chen DF, Zhang GQ: Chromosome-Scale Assembly of the Dendrobium nobile Genome Provides Insights Into the Molecular Mechanism of the Biosynthesis of the Medicinal Active Ingredient of Dendrobium. Front Genet. 2022 Mar 1;13:844622. doi: 10.3389/fgene.2022.844622. eCollection 2022. [PubMed:35299950 ]
- Lu AJ, Jiang Y, Wu J, Tan DP, Qin L, Lu YL, Qian Y, Bai CJ, Yang JY, Ling H, Shi JS, Yang Z, He YQ: Opposite trends of glycosides and alkaloids in Dendrobium nobile of different age based on UPLC-Q/TOF-MS combined with multivariate statistical analyses. Phytochem Anal. 2022 Jun;33(4):619-634. doi: 10.1002/pca.3115. Epub 2022 Mar 2. [PubMed:35238089 ]
- Wang SS, Liu JM, Sun J, Huang YT, Jin N, Li MM, Liang YT, Fan B, Wang FZ: Analysis of Endophytic Bacterial Diversity From Different Dendrobium Stems and Discovery of an Endophyte Produced Dendrobine-Type Sesquiterpenoid Alkaloids. Front Microbiol. 2022 Jan 5;12:775665. doi: 10.3389/fmicb.2021.775665. eCollection 2021. [PubMed:35069479 ]
- Qian X, Jin H, Chen Z, Dai Q, Sarsaiya S, Qin Y, Jia Q, Jin L, Chen J: Comparative Transcriptome Analysis of Genes Involved in Sesquiterpene Alkaloid Biosynthesis in Trichoderma longibrachiatum MD33 and UN32. Front Microbiol. 2021 Dec 15;12:800125. doi: 10.3389/fmicb.2021.800125. eCollection 2021. [PubMed:34975823 ]
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