Record Information |
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Version | 2.0 |
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Created at | 2022-09-05 08:17:21 UTC |
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Updated at | 2022-09-05 08:17:21 UTC |
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NP-MRD ID | NP0210463 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,3bs,4r,5s,5as,9as,9bs,11ar)-1-(furan-3-yl)-5-hydroxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate |
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Description | NIMONOL belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (1s,3bs,4r,5s,5as,9as,9bs,11ar)-1-(furan-3-yl)-5-hydroxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate is found in Azadirachta indica. It was first documented in 2009 (PMID: 19947185). Based on a literature review a small amount of articles have been published on NIMONOL (PMID: 33583331) (PMID: 24634075) (PMID: 31795367) (PMID: 24031718). |
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Structure | CC(=O)O[C@H]1[C@@H](O)[C@@H]2C(C)(C)C(=O)C=C[C@@]2(C)[C@@H]2CC[C@]3(C)[C@H](CC=C3[C@@]12C)C1=COC=C1 InChI=1S/C28H36O5/c1-16(29)33-24-22(31)23-25(2,3)21(30)10-13-27(23,5)20-9-12-26(4)18(17-11-14-32-15-17)7-8-19(26)28(20,24)6/h8,10-11,13-15,18,20,22-24,31H,7,9,12H2,1-6H3/t18-,20+,22+,23-,24+,26-,27+,28-/m1/s1 |
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Synonyms | Value | Source |
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7 alpha-Acetyl-17 alpha-(3-furyl)-6 alpha-hydroxy-4 alpha,4 beta,8 beta-trimethyl-5 alpha,18 alpha-androsta-1,14-dien-3-one | MeSH |
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Chemical Formula | C28H36O5 |
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Average Mass | 452.5910 Da |
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Monoisotopic Mass | 452.25627 Da |
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IUPAC Name | (1S,2S,7S,8S,9R,10S,14S,15R)-14-(furan-3-yl)-8-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-9-yl acetate |
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Traditional Name | (1S,2S,7S,8S,9R,10S,14S,15R)-14-(furan-3-yl)-8-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-9-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)O[C@H]1[C@@H](O)[C@@H]2C(C)(C)C(=O)C=C[C@@]2(C)[C@@H]2CC[C@]3(C)[C@H](CC=C3[C@@]12C)C1=COC=C1 |
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InChI Identifier | InChI=1S/C28H36O5/c1-16(29)33-24-22(31)23-25(2,3)21(30)10-13-27(23,5)20-9-12-26(4)18(17-11-14-32-15-17)7-8-19(26)28(20,24)6/h8,10-11,13-15,18,20,22-24,31H,7,9,12H2,1-6H3/t18-,20+,22+,23-,24+,26-,27+,28-/m1/s1 |
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InChI Key | GDMYRVKWBYREMU-XICJEYOKSA-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 limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Triterpenoids |
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Direct Parent | Limonoids |
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Alternative Parents | |
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Substituents | - Limonoid skeleton
- 17-furanylsteroid skeleton
- Steroid ester
- 3-oxo-5-beta-steroid
- Oxosteroid
- Hydroxysteroid
- 6-hydroxysteroid
- 3-oxosteroid
- 3-oxo-delta-1-steroid
- Steroid
- Delta-1-steroid
- Cyclohexenone
- Heteroaromatic compound
- Furan
- Cyclic alcohol
- Cyclic ketone
- Secondary alcohol
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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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