| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-04 07:32:52 UTC |
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| Updated at | 2022-09-04 07:32:53 UTC |
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| NP-MRD ID | NP0190806 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (2r,3r,4r,5r)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol |
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| Description | Codonopsinine belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. (2r,3r,4r,5r)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol is found in Codonopsis clematidea. (2r,3r,4r,5r)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol was first documented in 2015 (PMID: 25710030). Based on a literature review a small amount of articles have been published on Codonopsinine (PMID: 31347622) (PMID: 30777662) (PMID: 26883393) (PMID: 26771920). |
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| Structure | COC1=CC=C(C=C1)[C@@H]1[C@@H](O)[C@H](O)[C@@H](C)N1C InChI=1S/C13H19NO3/c1-8-12(15)13(16)11(14(8)2)9-4-6-10(17-3)7-5-9/h4-8,11-13,15-16H,1-3H3/t8-,11-,12-,13-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C13H19NO3 |
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| Average Mass | 237.2990 Da |
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| Monoisotopic Mass | 237.13649 Da |
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| IUPAC Name | (2R,3R,4R,5R)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol |
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| Traditional Name | (2R,3R,4R,5R)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diol |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=CC=C(C=C1)[C@@H]1[C@@H](O)[C@H](O)[C@@H](C)N1C |
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| InChI Identifier | InChI=1S/C13H19NO3/c1-8-12(15)13(16)11(14(8)2)9-4-6-10(17-3)7-5-9/h4-8,11-13,15-16H,1-3H3/t8-,11-,12-,13-/m1/s1 |
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| InChI Key | GJZNAEFHIYPPEM-HUXSOILUSA-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 phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Pyrrolidines |
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| Sub Class | Phenylpyrrolidines |
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| Direct Parent | Phenylpyrrolidines |
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| Alternative Parents | |
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| Substituents | - 2-phenylpyrrolidine
- Phenoxy compound
- Anisole
- Phenol ether
- Methoxybenzene
- Alkyl aryl ether
- Aralkylamine
- Monocyclic benzene moiety
- Benzenoid
- N-alkylpyrrolidine
- Pyrrole
- Secondary alcohol
- 1,2-aminoalcohol
- Tertiary aliphatic amine
- 1,2-diol
- Tertiary amine
- Azacycle
- Ether
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Amine
- Organic nitrogen compound
- Alcohol
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic 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 | - Pandey G, Laha R, Mondal PK: Heterocyclization involving benzylic C(sp(3))-H functionalization enabled by visible light photoredox catalysis. Chem Commun (Camb). 2019 Aug 21;55(65):9689-9692. doi: 10.1039/c9cc04287c. Epub 2019 Jul 26. [PubMed:31347622 ]
- El-Nezhawy AOH, Alrobaian M, Khames A, El-Badawy MF, Abdelwahab SF: Design and total synthesis of (-)-codonopsinine, (-)-codonopsine and codonopsinine analogues by O-(2-oxopyrrolidin-5-yl)trichloroacetimidate as amidoalkylating agent with improved antimicrobial activity via solid lipid nanoparticle formulations. Bioorg Med Chem. 2019 Apr 1;27(7):1263-1273. doi: 10.1016/j.bmc.2019.02.021. Epub 2019 Feb 13. [PubMed:30777662 ]
- Yamaguchi M, Itagaki D, Ueda H, Tokuyama H: Total syntheses of codonopsinine and 4-epi-codonopsinine via gold-mediated tandem-catalyzed pyrrole synthesis. J Antibiot (Tokyo). 2016 Apr;69(4):253-8. doi: 10.1038/ja.2016.13. Epub 2016 Feb 17. [PubMed:26883393 ]
- Lingamurthy M, Jagadeesh Y, Ramakrishna K, Rao BV: DDQ-Promoted Benzylic/Allylic sp(3) C-H Activation for the Stereoselective Intramolecular C-N Bond Formation: Applications to the Total Synthesis of (-)-Codonopsinine, (+)-5-epi-Codonopsinine, (+)-Radicamine B, and (-)-Codonopsinol. J Org Chem. 2016 Feb 19;81(4):1367-77. doi: 10.1021/acs.joc.5b02275. Epub 2016 Jan 29. [PubMed:26771920 ]
- Johari SA, Mohtar M, Mohammad SA, Sahdan R, Shaameri Z, Hamzah AS, Mohammat MF: In vitro inhibitory and cytotoxic activity of MFM 501, a novel codonopsinine derivative, against Methicillin-Resistant Staphylococcus aureus clinical isolates. Biomed Res Int. 2015;2015:823829. doi: 10.1155/2015/823829. Epub 2015 Feb 1. [PubMed:25710030 ]
- LOTUS database [Link]
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