| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-27 22:24:08 UTC |
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| Updated at | 2022-04-27 22:24:09 UTC |
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| NP-MRD ID | NP0050935 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (+)-Amurine |
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| Description | Amurine belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. (+)-Amurine is found in Elastostema sinuata, Meconopsis cambrica, Papaver auranticum, Papaver kerneri, Papaver nudicaule, Papaver nudicaule var. amurense, Papaver pilosum, Papaver radicatum, Papaver triniifolium, Roemeria refracta and Stephania aculeata. (+)-Amurine was first documented in 2002 (PMID: 12115607). Based on a literature review a small amount of articles have been published on Amurine (PMID: 33039968) (PMID: 17763104) (PMID: 12842145). |
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| Structure | COC1=C[C@]23CCN(C)[C@H](CC4=C2C=C2OCOC2=C4)C3=CC1=O InChI=1S/C19H19NO4/c1-20-4-3-19-9-18(22-2)15(21)7-13(19)14(20)5-11-6-16-17(8-12(11)19)24-10-23-16/h6-9,14H,3-5,10H2,1-2H3/t14-,19-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C19H19NO4 |
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| Average Mass | 325.3640 Da |
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| Monoisotopic Mass | 325.13141 Da |
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| IUPAC Name | (1R,12R)-16-methoxy-20-methyl-5,7-dioxa-20-azapentacyclo[10.5.3.0^{1,13}.0^{2,10}.0^{4,8}]icosa-2(10),3,8,13,16-pentaen-15-one |
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| Traditional Name | (1R,12R)-16-methoxy-20-methyl-5,7-dioxa-20-azapentacyclo[10.5.3.0^{1,13}.0^{2,10}.0^{4,8}]icosa-2(10),3,8,13,16-pentaen-15-one |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=C[C@]23CCN(C)[C@H](CC4=C2C=C2OCOC2=C4)C3=CC1=O |
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| InChI Identifier | InChI=1S/C19H19NO4/c1-20-4-3-19-9-18(22-2)15(21)7-13(19)14(20)5-11-6-16-17(8-12(11)19)24-10-23-16/h6-9,14H,3-5,10H2,1-2H3/t14-,19-/m1/s1 |
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| InChI Key | HTAGIZQYGRLQQX-AUUYWEPGSA-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 phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Phenanthrenes and derivatives |
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| Sub Class | Not Available |
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| Direct Parent | Phenanthrenes and derivatives |
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| Alternative Parents | |
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| Substituents | - Phenanthrene
- Benzazocine
- Isoquinolone
- Tetralin
- Benzodioxole
- Aralkylamine
- Piperidine
- Ketone
- Tertiary amine
- Tertiary aliphatic amine
- Cyclic ketone
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Azacycle
- Hydrocarbon derivative
- Amine
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Carbonyl group
- Organic nitrogen 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 | - Chen Y, Lu J, Li S, Zhang C, Yang Q, Hu B, Zhou C, Hong J, Jiang G, Yan S: Carnosol attenuates RANKL-induced osteoclastogenesis in vitro and LPS-induced bone loss. Int Immunopharmacol. 2020 Dec;89(Pt A):106978. doi: 10.1016/j.intimp.2020.106978. Epub 2020 Oct 8. [PubMed:33039968 ]
- Philipov S, Istatkova R, Yadamsurenghiin GO, Samdan J, Dangaa S: A new 8,14-dihydropromorphinane alkaloid from Papaver nudicaule L. Nat Prod Res. 2007 Jul 20;21(9):852-6. doi: 10.1080/14786410701494777. [PubMed:17763104 ]
- Blanchfield JT, Sands DP, Kennard CH, Byriel KA, Kitching W: Characterisation of alkaloids from some Australian Stephania (Menispermaceae) species. Phytochemistry. 2003 Jul;63(6):711-20. doi: 10.1016/s0031-9422(03)00240-1. [PubMed:12842145 ]
- Ishikawa S, Nagai S, Sato T, Akadegawa K, Yoneyama H, Zhang YY, Onai N, Matsushima K: Increased circulating CD11b+CD11c+ dendritic cells (DC) in aged BWF1 mice which can be matured by TNF-alpha into BLC/CXCL13-producing DC. Eur J Immunol. 2002 Jul;32(7):1881-7. doi: 10.1002/1521-4141(200207)32:7<1881::AID-IMMU1881>3.0.CO;2-Z. [PubMed:12115607 ]
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