Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 00:19:13 UTC |
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Updated at | 2022-09-11 00:19:13 UTC |
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NP-MRD ID | NP0307292 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (+)-armepavine |
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Description | (+)-Armepavine belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. (+)-armepavine is found in Artabotrys brachypetalus, Nelumbo nucifera and Roemeria refracta. It was first documented in 2019 (PMID: 31695616). Based on a literature review a significant number of articles have been published on (+)-Armepavine (PMID: 34903659) (PMID: 34139281) (PMID: 33596472) (PMID: 32503690). |
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Structure | COC1=CC2=C(C=C1OC)[C@H](CC1=CC=C(O)C=C1)N(C)CC2 InChI=1S/C19H23NO3/c1-20-9-8-14-11-18(22-2)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17,21H,8-10H2,1-3H3/t17-/m0/s1 |
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Synonyms | Value | Source |
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Armepavine | MeSH | Armepavine, (+-)-isomer | MeSH | Armepavine, (R)-isomer | MeSH | Armepavine, (S)-isomer | MeSH |
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Chemical Formula | C19H23NO3 |
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Average Mass | 313.3970 Da |
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Monoisotopic Mass | 313.16779 Da |
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IUPAC Name | 4-{[(1S)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenol |
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Traditional Name | 4-{[(1S)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl}phenol |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC2=C(C=C1OC)[C@H](CC1=CC=C(O)C=C1)N(C)CC2 |
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InChI Identifier | InChI=1S/C19H23NO3/c1-20-9-8-14-11-18(22-2)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17,21H,8-10H2,1-3H3/t17-/m0/s1 |
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InChI Key | ZBKFZIUKXTWQTP-KRWDZBQOSA-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 benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Isoquinolines and derivatives |
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Sub Class | Benzylisoquinolines |
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Direct Parent | Benzylisoquinolines |
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Alternative Parents | |
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Substituents | - Benzylisoquinoline
- Tetrahydroisoquinoline
- Anisole
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Aralkylamine
- Monocyclic benzene moiety
- Benzenoid
- Tertiary amine
- Tertiary aliphatic amine
- Azacycle
- Ether
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | - 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 ]
- Payne JT, Valentic TR, Smolke CD: Complete biosynthesis of the bisbenzylisoquinoline alkaloids guattegaumerine and berbamunine in yeast. Proc Natl Acad Sci U S A. 2021 Dec 21;118(51). pii: 2112520118. doi: 10.1073/pnas.2112520118. [PubMed:34903659 ]
- Zhou H, Hou T, Gao Z, Guo X, Wang C, Wang J, Liu Y, Liang X: Discovery of eight alkaloids with D1 and D2 antagonist activity in leaves of Nelumbo nucifera Gaertn. Using FLIPR assays. J Ethnopharmacol. 2021 Oct 5;278:114335. doi: 10.1016/j.jep.2021.114335. Epub 2021 Jun 15. [PubMed:34139281 ]
- Zhang Y, Li L, Zhang J, Lin T, Jiang Y, Liu B: Screening of hypolipidemic active components in Jiang-Zhi-Ning and its preliminary mechanism research based on "active contribution value" study. J Ethnopharmacol. 2021 May 23;272:113926. doi: 10.1016/j.jep.2021.113926. Epub 2021 Feb 14. [PubMed:33596472 ]
- Xu W, Chen S, Wang X, Wu H, Yamada H, Hirano T: Bisbenzylisoquinoline alkaloids and P-glycoprotein function: A structure activity relationship study. Bioorg Med Chem. 2020 Jun 15;28(12):115553. doi: 10.1016/j.bmc.2020.115553. Epub 2020 May 11. [PubMed:32503690 ]
- LOTUS database [Link]
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