| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-06 08:13:39 UTC |
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| Updated at | 2022-09-06 08:13:39 UTC |
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| NP-MRD ID | NP0228530 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (2s,3r,6s)-6-[(1e,3e,5e)-deca-1,3,5-trien-1-yl]-2-methylpiperidin-3-ol |
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| Description | Microcosamine A belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. (2s,3r,6s)-6-[(1e,3e,5e)-deca-1,3,5-trien-1-yl]-2-methylpiperidin-3-ol is found in Microcos paniculata. (2s,3r,6s)-6-[(1e,3e,5e)-deca-1,3,5-trien-1-yl]-2-methylpiperidin-3-ol was first documented in 2013 (PMID: 23327794). Based on a literature review a small amount of articles have been published on Microcosamine A (PMID: 30406652) (PMID: 34918520) (PMID: 27553201) (PMID: 26565783). |
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| Structure | CCCC\C=C\C=C\C=C\[C@@H]1CC[C@@H](O)[C@H](C)N1 InChI=1S/C16H27NO/c1-3-4-5-6-7-8-9-10-11-15-12-13-16(18)14(2)17-15/h6-11,14-18H,3-5,12-13H2,1-2H3/b7-6+,9-8+,11-10+/t14-,15+,16+/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C16H27NO |
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| Average Mass | 249.3980 Da |
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| Monoisotopic Mass | 249.20926 Da |
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| IUPAC Name | (2S,3R,6S)-6-[(1E,3E,5E)-deca-1,3,5-trien-1-yl]-2-methylpiperidin-3-ol |
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| Traditional Name | (2S,3R,6S)-6-[(1E,3E,5E)-deca-1,3,5-trien-1-yl]-2-methylpiperidin-3-ol |
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| CAS Registry Number | Not Available |
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| SMILES | CCCC\C=C\C=C\C=C\[C@@H]1CC[C@@H](O)[C@H](C)N1 |
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| InChI Identifier | InChI=1S/C16H27NO/c1-3-4-5-6-7-8-9-10-11-15-12-13-16(18)14(2)17-15/h6-11,14-18H,3-5,12-13H2,1-2H3/b7-6+,9-8+,11-10+/t14-,15+,16+/m0/s1 |
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| InChI Key | LSCWHIBYDGDOLC-CCORAGHZSA-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 piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Piperidines |
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| Sub Class | Not Available |
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| Direct Parent | Piperidines |
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| Alternative Parents | |
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| Substituents | - Piperidine
- Secondary alcohol
- 1,2-aminoalcohol
- Azacycle
- Secondary amine
- Secondary aliphatic amine
- Organic nitrogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Amine
- Alcohol
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic 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 | - Macha L, Ha HJ: Total Synthesis and Absolute Stereochemical Assignment of Microgrewiapine A and Its Stereoisomers. J Org Chem. 2019 Jan 4;84(1):94-103. doi: 10.1021/acs.joc.8b02342. Epub 2018 Nov 16. [PubMed:30406652 ]
- Still PC, Yi B, Gonzalez-Cestari TF, Pan L, Pavlovicz RE, Chai HB, Ninh TN, Li C, Soejarto DD, McKay DB, Kinghorn AD: Alkaloids from Microcos paniculata with cytotoxic and nicotinic receptor antagonistic activities. J Nat Prod. 2013 Feb 22;76(2):243-9. doi: 10.1021/np3007414. Epub 2013 Jan 17. [PubMed:23327794 ]
- Davies SG, Fletcher AM, Roberts PM, Taylor CE, Thomson JE: Synthesis and Configuration of O-Acetyl Microgrewiapine A: Phantomization of O-Acetyl 6-epi-Microgrewiapine A. J Nat Prod. 2022 Jan 28;85(1):306-312. doi: 10.1021/acs.jnatprod.1c00847. Epub 2021 Dec 17. [PubMed:34918520 ]
- Zhang G, Zhang N, Xu L, Wu HT, Chen D, Lin QH, Luo LZ: A new piperidine alkaloid from the leaves of Microcos paniculata L. Nat Prod Res. 2017 Jan;31(2):169-174. doi: 10.1080/14786419.2016.1224868. Epub 2016 Aug 24. [PubMed:27553201 ]
- Raji Reddy C, Latha B, Warudikar K, Singarapu KK: Total synthesis of a piperidine alkaloid, microcosamine A. Org Biomol Chem. 2016 Jan 7;14(1):251-8. doi: 10.1039/c5ob02085a. Epub 2015 Nov 13. [PubMed:26565783 ]
- LOTUS database [Link]
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