| Record Information |
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| Version | 2.0 |
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| Created at | 2021-06-19 21:39:42 UTC |
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| Updated at | 2021-06-29 23:58:07 UTC |
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| NP-MRD ID | NP0030263 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Nepetaefolin |
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| Provided By | JEOL Database |
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| Description | (1''S,3R,3''R,5'S,5''R,6''R,7''S)-7''-methyl-8''-oxo-2H-trispiro[furan-3,2'-oxolane-5',2''-[9]oxatricyclo[5.3.3.0¹,⁶]Tridecane-3'',2'''-oxirane]-5''-yl acetate belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. Nepetaefolin is found in Leonotis nepetaefolia and Leonotis ocymifolia. Nepetaefolin was first documented in 2003 (Hussein, A. A., et al.). Based on a literature review very few articles have been published on (1''S,3R,3''R,5'S,5''R,6''R,7''S)-7''-methyl-8''-oxo-2H-trispiro[furan-3,2'-oxolane-5',2''-[9]oxatricyclo[5.3.3.0¹,⁶]Tridecane-3'',2'''-oxirane]-5''-yl acetate. |
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| Structure | [H]C1=C([H])[C@@]2(O[C@]3(C([H])([H])C2([H])[H])[C@@]2(OC2([H])[H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]2([H])[C@]4(C(=O)OC([H])([H])[C@@]32C([H])([H])C([H])([H])C4([H])[H])C([H])([H])[H])C([H])([H])O1 InChI=1S/C22H28O7/c1-14(23)28-15-10-21(13-27-21)22(7-6-19(29-22)8-9-25-11-19)20-5-3-4-18(2,16(15)20)17(24)26-12-20/h8-9,15-16H,3-7,10-13H2,1-2H3/t15-,16+,18+,19-,20-,21-,22+/m1/s1 |
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| Synonyms | | Value | Source |
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| (1''S,3R,3''r,5's,5''r,6''r,7''s)-7''-methyl-8''-oxo-2H-trispiro[furan-3,2'-oxolane-5',2''-[9]oxatricyclo[5.3.3.0,]tridecane-3'',2'''-oxirane]-5''-yl acetic acid | Generator |
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| Chemical Formula | C22H28O7 |
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| Average Mass | 404.4590 Da |
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| Monoisotopic Mass | 404.18350 Da |
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| IUPAC Name | (1''S,3R,3''R,5'S,5''R,6''R,7''S)-7''-methyl-8''-oxo-2H-trispiro[furan-3,2'-oxolane-5',2''-[9]oxatricyclo[5.3.3.0^{1,6}]tridecane-3'',2'''-oxirane]-5''-yl acetate |
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| Traditional Name | (1''S,3R,3''R,5'S,5''R,6''R,7''S)-7''-methyl-8''-oxo-2H-trispiro[furan-3,2'-oxolane-5',2''-[9]oxatricyclo[5.3.3.0^{1,6}]tridecane-3'',2'''-oxirane]-5''-yl acetate |
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| CAS Registry Number | Not Available |
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| SMILES | [H]C1=C([H])[C@@]2(O[C@]3(C([H])([H])C2([H])[H])[C@@]2(OC2([H])[H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]2([H])[C@]4(C(=O)OC([H])([H])[C@@]32C([H])([H])C([H])([H])C4([H])[H])C([H])([H])[H])C([H])([H])O1 |
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| InChI Identifier | InChI=1S/C22H28O7/c1-14(23)28-15-10-21(13-27-21)22(7-6-19(29-22)8-9-25-11-19)20-5-3-4-18(2,16(15)20)17(24)26-12-20/h8-9,15-16H,3-7,10-13H2,1-2H3/t15-,16+,18+,19-,20-,21-,22+/m1/s1 |
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| InChI Key | ITQNNYKKNNEJKM-WPTALCCWSA-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, 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, 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, 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, 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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| 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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| Leonotis nepetaefolia | Plant | | | Leonotis ocymifolia | JEOL database | - Hussein, A. A., et al, Magn. Reson. Chem. 41, 147 (2003)
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Lactones |
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| Sub Class | Delta valerolactones |
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| Direct Parent | Delta valerolactones |
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| Alternative Parents | |
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| Substituents | - Delta_valerolactone
- Delta valerolactone
- Oxane
- Dicarboxylic acid or derivatives
- Tetrahydrofuran
- Dihydrofuran
- Carboxylic acid ester
- Oxacycle
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic 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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