Record Information |
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Version | 1.0 |
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Created at | 2022-09-10 02:43:58 UTC |
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Updated at | 2022-09-10 02:43:58 UTC |
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NP-MRD ID | NP0294271 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | [5-(acetyloxy)-4-[6-(formyloxy)-1-(furan-3-yl)-3a-hydroxy-7-[(2-hydroxy-3-methylpentanoyl)oxy]-7a-methyl-4-methylidene-3-oxo-tetrahydro-1h-inden-5-yl]-2-(hydroxymethyl)-2,4-dimethyl-7-oxooxepan-3-yl]acetic acid |
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Description | 2-[5-(Acetyloxy)-4-[6-(formyloxy)-1-(furan-3-yl)-3a-hydroxy-7-[(2-hydroxy-3-methylpentanoyl)oxy]-7a-methyl-4-methylidene-3-oxo-octahydro-1H-inden-5-yl]-2-(hydroxymethyl)-2,4-dimethyl-7-oxooxepan-3-yl]acetic acid 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. [5-(acetyloxy)-4-[6-(formyloxy)-1-(furan-3-yl)-3a-hydroxy-7-[(2-hydroxy-3-methylpentanoyl)oxy]-7a-methyl-4-methylidene-3-oxo-tetrahydro-1h-inden-5-yl]-2-(hydroxymethyl)-2,4-dimethyl-7-oxooxepan-3-yl]acetic acid is found in Aphanamixis polystachya. 2-[5-(Acetyloxy)-4-[6-(formyloxy)-1-(furan-3-yl)-3a-hydroxy-7-[(2-hydroxy-3-methylpentanoyl)oxy]-7a-methyl-4-methylidene-3-oxo-octahydro-1H-inden-5-yl]-2-(hydroxymethyl)-2,4-dimethyl-7-oxooxepan-3-yl]acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CCC(C)C(O)C(=O)OC1C(OC=O)C(C(=C)C2(O)C(=O)CC(C3=COC=C3)C12C)C1(C)C(CC(=O)OC(C)(CO)C1CC(O)=O)OC(C)=O InChI=1S/C35H46O15/c1-8-17(2)28(43)31(44)49-30-29(47-16-37)27(18(3)35(45)23(39)11-21(34(30,35)7)20-9-10-46-14-20)33(6)22(12-25(40)41)32(5,15-36)50-26(42)13-24(33)48-19(4)38/h9-10,14,16-17,21-22,24,27-30,36,43,45H,3,8,11-13,15H2,1-2,4-7H3,(H,40,41) |
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Synonyms | Value | Source |
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2-[5-(Acetyloxy)-4-[6-(formyloxy)-1-(furan-3-yl)-3a-hydroxy-7-[(2-hydroxy-3-methylpentanoyl)oxy]-7a-methyl-4-methylidene-3-oxo-octahydro-1H-inden-5-yl]-2-(hydroxymethyl)-2,4-dimethyl-7-oxooxepan-3-yl]acetate | Generator |
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Chemical Formula | C35H46O15 |
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Average Mass | 706.7380 Da |
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Monoisotopic Mass | 706.28367 Da |
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IUPAC Name | 2-[5-(acetyloxy)-4-[6-(formyloxy)-1-(furan-3-yl)-3a-hydroxy-7-[(2-hydroxy-3-methylpentanoyl)oxy]-7a-methyl-4-methylidene-3-oxo-octahydro-1H-inden-5-yl]-2-(hydroxymethyl)-2,4-dimethyl-7-oxooxepan-3-yl]acetic acid |
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Traditional Name | [5-(acetyloxy)-4-[6-(formyloxy)-1-(furan-3-yl)-3a-hydroxy-7-[(2-hydroxy-3-methylpentanoyl)oxy]-7a-methyl-4-methylidene-3-oxo-tetrahydro-1H-inden-5-yl]-2-(hydroxymethyl)-2,4-dimethyl-7-oxooxepan-3-yl]acetic acid |
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CAS Registry Number | Not Available |
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SMILES | CCC(C)C(O)C(=O)OC1C(OC=O)C(C(=C)C2(O)C(=O)CC(C3=COC=C3)C12C)C1(C)C(CC(=O)OC(C)(CO)C1CC(O)=O)OC(C)=O |
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InChI Identifier | InChI=1S/C35H46O15/c1-8-17(2)28(43)31(44)49-30-29(47-16-37)27(18(3)35(45)23(39)11-21(34(30,35)7)20-9-10-46-14-20)33(6)22(12-25(40)41)32(5,15-36)50-26(42)13-24(33)48-19(4)38/h9-10,14,16-17,21-22,24,27-30,36,43,45H,3,8,11-13,15H2,1-2,4-7H3,(H,40,41) |
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InChI Key | BKEMYFWKZCXFTC-UHFFFAOYSA-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
- Pentacarboxylic acid or derivatives
- Caprolactone
- Fatty acid ester
- Oxepane
- Monosaccharide
- Fatty acyl
- Cyclic alcohol
- Furan
- Heteroaromatic compound
- Tertiary alcohol
- Lactone
- Ketone
- Carboxylic acid ester
- Secondary alcohol
- Oxacycle
- Carboxylic acid
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Primary alcohol
- Carbonyl group
- 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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