| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-29 01:21:17 UTC |
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| Updated at | 2022-04-29 01:21:17 UTC |
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| NP-MRD ID | NP0080317 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (+)-Vellosimine |
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| Description | Vellosimine belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. Vellosimine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (+)-Vellosimine is found in Alstonia yunnanensis, Rauvolfia verticillata , Rauvolfia serpentina , Rauvolfia verticillata var.hainanensis and Rauwolfia verticillata. (+)-Vellosimine was first documented in 2007 (PMID: 17217288). Based on a literature review a small amount of articles have been published on vellosimine (PMID: 33783073) (PMID: 28812370) (PMID: 25346454) (PMID: 20392128). |
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| Structure | C\C=C1\CN2[C@H]3CC4=C(NC5=CC=CC=C45)[C@@H]2C[C@@H]1[C@H]3C=O InChI=1S/C19H20N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,10,13,15,17-18,20H,7-9H2,1H3/b11-2-/t13-,15+,17-,18-/m0/s1 |
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| Synonyms | | Value | Source |
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| (+)-Vellosimine | ChEBI |
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| Chemical Formula | C19H20N2O |
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| Average Mass | 292.3820 Da |
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| Monoisotopic Mass | 292.15756 Da |
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| IUPAC Name | (1S,12S,13R,14R,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde |
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| Traditional Name | (1S,12S,13R,14R,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde |
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| CAS Registry Number | Not Available |
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| SMILES | C\C=C1\CN2[C@H]3CC4=C(NC5=CC=CC=C45)[C@@H]2C[C@@H]1[C@H]3C=O |
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| InChI Identifier | InChI=1S/C19H20N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,10,13,15,17-18,20H,7-9H2,1H3/b11-2-/t13-,15+,17-,18-/m0/s1 |
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| InChI Key | MHASSCPGKAMILD-VICVVEARSA-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 macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Macroline alkaloids |
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| Sub Class | Not Available |
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| Direct Parent | Macroline alkaloids |
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| Alternative Parents | |
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| Substituents | - Macroline skeleton
- Sarpagine-skeleton
- Vobasan skeleton
- Beta-carboline
- Pyridoindole
- 3-alkylindole
- Indole
- Indole or derivatives
- Quinuclidine
- Aralkylamine
- Benzenoid
- Piperidine
- Heteroaromatic compound
- Pyrrole
- Tertiary aliphatic amine
- Tertiary amine
- Organoheterocyclic compound
- Azacycle
- Organic nitrogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Aldehyde
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic 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 | - Yang Z, Tan Q, Jiang Y, Yang J, Su X, Qiao Z, Zhou W, He L, Qiu H, Zhang M: Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids. Angew Chem Int Ed Engl. 2021 Jun 1;60(23):13105-13111. doi: 10.1002/anie.202102416. Epub 2021 May 5. [PubMed:33783073 ]
- Ebeh Messanga R, Dominique Serge NB, Abouem A Zintchem A, Norbert MNI, Esther Del Florence MN, Patrick Herve BD, Maximilienne Ascension N, Alex De Theodore A, Dieudonne Emmanuel P, Christian G B, Koert U: Rauvolfianine, a new antimycobacterial glyceroglycolipid and other constituents from Rauvolfia caffra. Sond (Apocynaceae). Nat Prod Res. 2018 Aug;32(16):1971-1976. doi: 10.1080/14786419.2017.1356832. Epub 2017 Aug 16. [PubMed:28812370 ]
- Kruger S, Gaich T: Enantioselective, protecting-group-free total synthesis of sarpagine alkaloids--a generalized approach. Angew Chem Int Ed Engl. 2015 Jan 2;54(1):315-7. doi: 10.1002/anie.201407280. Epub 2014 Oct 24. [PubMed:25346454 ]
- Yin W, Kabir MS, Wang Z, Rallapalli SK, Ma J, Cook JM: Enantiospecific total synthesis of the important biogenetic intermediates along the ajmaline pathway, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epivellosimine and macusine A. J Org Chem. 2010 May 21;75(10):3339-49. doi: 10.1021/jo100279w. [PubMed:20392128 ]
- Yin W, Ma J, Rivas FM, Cook JM: First enantiospecific total synthesis of the important biogenetic intermediates, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epi-vellosimine and macusine A. Org Lett. 2007 Jan 18;9(2):295-8. doi: 10.1021/ol062762q. [PubMed:17217288 ]
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