Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 13:04:48 UTC |
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Updated at | 2022-04-28 13:04:48 UTC |
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NP-MRD ID | NP0068070 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (+)-Limacusine 2-alpha-N-oxide |
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Description | Limacusine 2-oxide belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. (+)-Limacusine 2-alpha-N-oxide is found in Anisocycla jollyana (Pierre) Diels. Based on a literature review very few articles have been published on Limacusine 2-oxide. |
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Structure | COC1=C(O)C2=C3[C@@H](CC4=CC=C(OC5=C(OC)C=CC(C[C@H]6N(C)CCC7=CC(OC)=C(O2)C=C67)=C5)C=C4)N(C)(=O)CCC3=C1 InChI=1S/C37H40N2O7/c1-38-14-12-24-19-31(43-4)33-21-27(24)28(38)16-23-8-11-30(42-3)32(18-23)45-26-9-6-22(7-10-26)17-29-35-25(13-15-39(29,2)41)20-34(44-5)36(40)37(35)46-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29-,39?/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C37H40N2O7 |
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Average Mass | 624.7340 Da |
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Monoisotopic Mass | 624.28355 Da |
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IUPAC Name | (1R,14R)-21-hydroxy-6,20,25-trimethoxy-15,30-dimethyl-8,23-dioxa-15lambda5,30-diazaheptacyclo[22.6.2.2^{9,12}.1^{3,7}.1^{14,18}.0^{27,31}.0^{22,33}]hexatriaconta-3(36),4,6,9,11,18,20,22(33),24,26,31,34-dodecaen-15-one |
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Traditional Name | (1R,14R)-21-hydroxy-6,20,25-trimethoxy-15,30-dimethyl-8,23-dioxa-15lambda5,30-diazaheptacyclo[22.6.2.2^{9,12}.1^{3,7}.1^{14,18}.0^{27,31}.0^{22,33}]hexatriaconta-3(36),4,6,9,11,18,20,22(33),24,26,31,34-dodecaen-15-one |
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CAS Registry Number | Not Available |
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SMILES | COC1=C(O)C2=C3[C@@H](CC4=CC=C(OC5=C(OC)C=CC(C[C@H]6N(C)CCC7=CC(OC)=C(O2)C=C67)=C5)C=C4)N(C)(=O)CCC3=C1 |
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InChI Identifier | InChI=1S/C37H40N2O7/c1-38-14-12-24-19-31(43-4)33-21-27(24)28(38)16-23-8-11-30(42-3)32(18-23)45-26-9-6-22(7-10-26)17-29-35-25(13-15-39(29,2)41)20-34(44-5)36(40)37(35)46-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29-,39?/m1/s1 |
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InChI Key | BMNWTEXRVYGPQW-FYMKWHHZSA-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 lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Not Available |
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Sub Class | Not Available |
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Direct Parent | Lignans, neolignans and related compounds |
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Alternative Parents | |
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Substituents | - Oxyneolignan skeleton
- Diaryl ether
- Tetrahydroisoquinoline
- Anisole
- Phenol ether
- Alkyl aryl ether
- Phenol
- Aralkylamine
- Benzenoid
- Trialkyl amine oxide
- Tertiary amine
- Tertiary aliphatic amine
- Trisubstituted n-oxide
- N-oxide
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Ether
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Amine
- Organic zwitterion
- Organic salt
- 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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