Record Information |
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Version | 1.0 |
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Created at | 2021-06-20 18:17:58 UTC |
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Updated at | 2021-06-30 00:05:08 UTC |
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NP-MRD ID | NP0034622 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | pronuciferine |
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Provided By | JEOL Database |
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Description | (+)-Pronuciferine, also known as milthanthine or N-methylstepharine, belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol (+)-pronuciferine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. pronuciferine is found in Berberis coletioides, Berberis montana, Cissampelos capensis, Cocculus laurifolius, Glossocalyx brevipes, Gyrocarpus americanus, Hypserpa nitida, Meconopsis cambrica, Peumus boldus, Plumula nelumbensis and Uvaria dulcis. It was first documented in 1968 (PMID: 5683993). Based on a literature review a significant number of articles have been published on (+)-pronuciferine (PMID: 19469512) (PMID: 32852096) (PMID: 31707550) (PMID: 31695616) (PMID: 30189375) (PMID: 29087605). |
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Structure | [H]C1=C([H])C2(C([H])=C([H])C1=O)C1=C3C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])C([H])([H])N(C([H])([H])[H])[C@]3([H])C2([H])[H] InChI=1S/C19H21NO3/c1-20-9-6-12-10-15(22-2)18(23-3)17-16(12)14(20)11-19(17)7-4-13(21)5-8-19/h4-5,7-8,10,14H,6,9,11H2,1-3H3/t14-/m1/s1 |
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Synonyms | Value | Source |
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Milthanthine | ChEBI | N,O-Dimethylcrotonosine | ChEBI | N-Methylstepharine | ChEBI | Pronuciferin | ChEBI |
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Chemical Formula | C19H21NO3 |
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Average Mass | 311.3810 Da |
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Monoisotopic Mass | 311.15214 Da |
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IUPAC Name | (4'R)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(12'),2,5,8',10'-pentaen-4-one |
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Traditional Name | (4'R)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(12'),2,5,8',10'-pentaen-4-one |
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CAS Registry Number | Not Available |
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SMILES | [H]C1=C([H])C2(C([H])=C([H])C1=O)C1=C3C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])C([H])([H])N(C([H])([H])[H])[C@]3([H])C2([H])[H] |
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InChI Identifier | InChI=1S/C19H21NO3/c1-20-9-6-12-10-15(22-2)18(23-3)17-16(12)14(20)11-19(17)7-4-13(21)5-8-19/h4-5,7-8,10,14H,6,9,11H2,1-3H3/t14-/m1/s1 |
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InChI Key | WUYQEGNOQLRQAQ-CQSZACIVSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| 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, 100 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, chcl3, 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 proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Proaporphines |
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Sub Class | Not Available |
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Direct Parent | Proaporphines |
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Alternative Parents | |
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Substituents | - Proaporphine
- Tetrahydroisoquinoline
- Indane
- Anisole
- Alkyl aryl ether
- Aralkylamine
- Benzenoid
- Ketone
- Tertiary amine
- Cyclic ketone
- Tertiary aliphatic amine
- Ether
- Azacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organonitrogen compound
- Amine
- Hydrocarbon derivative
- Organopnictogen compound
- Carbonyl group
- Organic nitrogen compound
- Organic oxide
- Organic oxygen compound
- 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 | - Fajardo V, Araya M, Cuadra P, Oyarzun A, Gallardo A, Cueto M, Diaz-Marrero AR, Darias J, Villarroel L, Alvarez C, Mora-Perez Y, Joseph-Nathan P: Pronuciferine N-oxide, a proaporphine N-oxide alkaloid from Berberis coletioides. J Nat Prod. 2009 Jul;72(7):1355-6. doi: 10.1021/np9000976. [PubMed:19469512 ]
- Bernauer K: [On the synthesis of pronuciferin and some other proaporphine alkaloids]. Helv Chim Acta. 1968 Jul 10;51(5):1119-29. doi: 10.1002/hlca.19680510514. [PubMed:5683993 ]
- Bayazeid O, Nemutlu E, Eylem CC, Yalcin FN: Neuroactivity of naturally occurring proaporphine alkaloid, pronuciferine. J Biochem Mol Toxicol. 2020 Dec;34(12):e22601. doi: 10.1002/jbt.22601. Epub 2020 Aug 27. [PubMed:32852096 ]
- Yano M, Nakashima S, Oda Y, Nakamura S, Matsuda H: BBB-permeable aporphine-type alkaloids in Nelumbo nucifera flowers with accelerative effects on neurite outgrowth in PC-12 cells. J Nat Med. 2020 Jan;74(1):212-218. doi: 10.1007/s11418-019-01368-7. Epub 2019 Nov 9. [PubMed:31707550 ]
- Zou S, Ge Y, Chen X, Li J, Yang X, Wang H, Gao X, Chang YX: Simultaneous Determination of Five Alkaloids by HPLC-MS/MS Combined With Micro-SPE in Rat Plasma and Its Application to Pharmacokinetics After Oral Administration of Lotus Leaf Extract. Front Pharmacol. 2019 Oct 22;10:1252. doi: 10.3389/fphar.2019.01252. eCollection 2019. [PubMed:31695616 ]
- Bayazeid O, Eylem CC, Recber T, Yalcin FN, Kir S, Nemutlu E: An LC-ESI-MS/MS method for the simultaneous determination of pronuciferine and roemerine in some Papaver species. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Oct 1;1096:223-227. doi: 10.1016/j.jchromb.2018.08.020. Epub 2018 Aug 21. [PubMed:30189375 ]
- Wu N, Xie H, Fang Y, Liu Y, Xi X, Chu Q, Dong G, Lan T, Wei Y: Isolation and purification of alkaloids from lotus leaves by ionic-liquid-modified high-speed countercurrent chromatography. J Sep Sci. 2018 Jan;41(2):571-577. doi: 10.1002/jssc.201700851. Epub 2017 Dec 5. [PubMed:29087605 ]
- Morikawa T, Kitagawa N, Tanabe G, Ninomiya K, Okugawa S, Motai C, Kamei I, Yoshikawa M, Lee IJ, Muraoka O: Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity. Molecules. 2016 Jul 19;21(7). pii: molecules21070930. doi: 10.3390/molecules21070930. [PubMed:27447599 ]
- Fajardo, V., et al. (2009). Fajardo, V., et al, J. Nat. Prod. 72, 1355 (2009). J. Nat. Prod..
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