Record Information |
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Version | 1.0 |
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Created at | 2021-06-20 19:16:06 UTC |
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Updated at | 2021-06-30 00:07:21 UTC |
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NP-MRD ID | NP0035970 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (+)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,7'-epoxy lignan+ |
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Provided By | JEOL Database |
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Description | (+)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,7'-epoxylignan-9,9'-diol belongs to the class of organic compounds known as 7,7'-epoxylignans. These are lignans with a structure based on a 2,5-diaryl-3, 4-dimethyltetrahydrofuran skeleton (+)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,7'-epoxylignan-9,9'-diol 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. (+)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,7'-epoxy lignan+ is found in Sinocalamus affinis. It was first documented in 2011 (PMID: 21469695). Based on a literature review very few articles have been published on (+)-(7R,7'R,8S,8'S)-4'-hydroxy-3,3',4,5,5'-pentamethoxy-7,7'-epoxylignan-9,9'-diol (PMID: 24010288). |
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Structure | [H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1OC([H])([H])[H])[C@]1([H])O[C@@]([H])(C2=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C2[H])[C@]([H])(C([H])([H])O[H])[C@@]1([H])C([H])([H])O[H] InChI=1S/C23H30O9/c1-27-16-6-12(7-17(28-2)20(16)26)21-14(10-24)15(11-25)22(32-21)13-8-18(29-3)23(31-5)19(9-13)30-4/h6-9,14-15,21-22,24-26H,10-11H2,1-5H3/t14-,15-,21+,22+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C23H30O9 |
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Average Mass | 450.4840 Da |
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Monoisotopic Mass | 450.18898 Da |
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IUPAC Name | 4-[(2R,3S,4S,5R)-3,4-bis(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)oxolan-2-yl]-2,6-dimethoxyphenol |
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Traditional Name | 4-[(2R,3S,4S,5R)-3,4-bis(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)oxolan-2-yl]-2,6-dimethoxyphenol |
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CAS Registry Number | Not Available |
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SMILES | [H]OC1=C(OC([H])([H])[H])C([H])=C(C([H])=C1OC([H])([H])[H])[C@]1([H])O[C@@]([H])(C2=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C2[H])[C@]([H])(C([H])([H])O[H])[C@@]1([H])C([H])([H])O[H] |
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InChI Identifier | InChI=1S/C23H30O9/c1-27-16-6-12(7-17(28-2)20(16)26)21-14(10-24)15(11-25)22(32-21)13-8-18(29-3)23(31-5)19(9-13)30-4/h6-9,14-15,21-22,24-26H,10-11H2,1-5H3/t14-,15-,21+,22+/m1/s1 |
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InChI Key | TXNROPYUDLUIHU-SDVFQCAASA-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, 600 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Species Name | Source | Reference |
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Sinocalamus affinis | JEOL database | - Xiong, L., et al, J. Nat. Prod. 74, 1188 (2011)
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 7,7'-epoxylignans. These are lignans with a structure based on a 2,5-diaryl-3, 4-dimethyltetrahydrofuran skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Furanoid lignans |
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Sub Class | Tetrahydrofuran lignans |
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Direct Parent | 7,7'-epoxylignans |
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Alternative Parents | |
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Substituents | - 7,7p-epoxylignan
- Dibenzylbutane lignan skeleton
- Methoxyphenol
- Dimethoxybenzene
- M-dimethoxybenzene
- Anisole
- Methoxybenzene
- Phenoxy compound
- Phenol ether
- Alkyl aryl ether
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Tetrahydrofuran
- Ether
- Dialkyl ether
- Organoheterocyclic compound
- Oxacycle
- Organooxygen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Primary alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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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