Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 13:29:07 UTC |
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Updated at | 2022-09-12 13:29:07 UTC |
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NP-MRD ID | NP0329256 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 6-(but-2-en-2-yl)-3,21',24'-trihydroxy-5,11',13',22'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-4-yl 2-methylpropanoate |
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Description | 6-(But-2-en-2-yl)-3,21',24'-trihydroxy-5,11',13',22'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]Pentacosane]-10',14',16',22'-tetraen-4-yl 2-methylpropanoate belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.G. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species. 6-(But-2-en-2-yl)-3,21',24'-trihydroxy-5,11',13',22'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]Pentacosane]-10',14',16',22'-tetraen-4-yl 2-methylpropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CC=C(C)C1OC2(CC3CC(CC=C(C)CC(C)C=CC=C4COC5C(O)C(C)=CC(C(=O)O3)C45O)O2)C(O)C(OC(=O)C(C)C)C1C InChI=1S/C38H54O10/c1-9-23(6)31-25(8)32(46-35(41)20(2)3)33(40)37(48-31)18-28-17-27(47-37)14-13-22(5)15-21(4)11-10-12-26-19-44-34-30(39)24(7)16-29(36(42)45-28)38(26,34)43/h9-13,16,20-21,25,27-34,39-40,43H,14-15,17-19H2,1-8H3 |
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Synonyms | Value | Source |
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6-(But-2-en-2-yl)-3,21',24'-trihydroxy-5,11',13',22'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1,.0,]pentacosane]-10',14',16',22'-tetraen-4-yl 2-methylpropanoic acid | Generator | 6-(But-2-en-2-yl)-3,21',24'-trihydroxy-5,11',13',22'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-4-yl 2-methylpropanoic acid | Generator |
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Chemical Formula | C38H54O10 |
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Average Mass | 670.8400 Da |
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Monoisotopic Mass | 670.37170 Da |
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IUPAC Name | 6-(but-2-en-2-yl)-3,21',24'-trihydroxy-5,11',13',22'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-4-yl 2-methylpropanoate |
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Traditional Name | 6-(but-2-en-2-yl)-3,21',24'-trihydroxy-5,11',13',22'-tetramethyl-2'-oxo-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-4-yl 2-methylpropanoate |
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CAS Registry Number | Not Available |
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SMILES | CC=C(C)C1OC2(CC3CC(CC=C(C)CC(C)C=CC=C4COC5C(O)C(C)=CC(C(=O)O3)C45O)O2)C(O)C(OC(=O)C(C)C)C1C |
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InChI Identifier | InChI=1S/C38H54O10/c1-9-23(6)31-25(8)32(46-35(41)20(2)3)33(40)37(48-31)18-28-17-27(47-37)14-13-22(5)15-21(4)11-10-12-26-19-44-34-30(39)24(7)16-29(36(42)45-28)38(26,34)43/h9-13,16,20-21,25,27-34,39-40,43H,14-15,17-19H2,1-8H3 |
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InChI Key | BRUOADCBAUEUIC-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 | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.G. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Macrolides and analogues |
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Sub Class | Milbemycins |
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Direct Parent | Milbemycins |
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Alternative Parents | |
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Substituents | - Milbemycin
- Ketal
- Dicarboxylic acid or derivatives
- Monosaccharide
- Oxane
- Tetrahydrofuran
- Tertiary alcohol
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Acetal
- Carboxylic acid derivative
- Dialkyl ether
- Ether
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Organic oxide
- Carbonyl group
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Organooxygen compound
- 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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