Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 06:22:56 UTC |
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Updated at | 2022-04-28 06:22:56 UTC |
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NP-MRD ID | NP0061625 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 13beta,29-Dihydroxymilbemycin A4 |
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Description | (1'S,2S,4'R,5R,6S,8'S,10'E,12'S,13'R,14'E,20'R,21'S,24'R)-6-ethyl-12',21',24'-trihydroxy-11'-(hydroxymethyl)-5,13',22'-trimethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]Pentacosane]-10',14',16',22'-tetraen-2'-one 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. 13beta,29-Dihydroxymilbemycin A4 is found in Streptomyces cavourensis and Streptomyces cavourensis SANK 67386. Based on a literature review very few articles have been published on (1'S,2S,4'R,5R,6S,8'S,10'E,12'S,13'R,14'E,20'R,21'S,24'R)-6-ethyl-12',21',24'-trihydroxy-11'-(hydroxymethyl)-5,13',22'-trimethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]Pentacosane]-10',14',16',22'-tetraen-2'-one. |
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Structure | CC[C@@H]1O[C@@]2(CC[C@H]1C)C[C@H]1C[C@H](C\C=C(CO)\[C@@H](O)[C@H](C)\C=C\C=C3/CO[C@@H]4[C@@H](O)C(C)=C[C@H](C(=O)O1)[C@@]34O)O2 InChI=1S/C32H46O9/c1-5-26-18(2)11-12-31(41-26)15-24-14-23(40-31)10-9-21(16-33)27(34)19(3)7-6-8-22-17-38-29-28(35)20(4)13-25(30(36)39-24)32(22,29)37/h6-9,13,18-19,23-29,33-35,37H,5,10-12,14-17H2,1-4H3/b7-6+,21-9+,22-8+/t18-,19-,23+,24-,25-,26+,27+,28+,29-,31+,32+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C32H46O9 |
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Average Mass | 574.7110 Da |
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Monoisotopic Mass | 574.31418 Da |
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IUPAC Name | (1'S,2S,4'R,5R,6S,8'S,10'E,12'S,13'R,14'E,16'E,20'R,21'S,24'R)-6-ethyl-12',21',24'-trihydroxy-11'-(hydroxymethyl)-5,13',22'-trimethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-2'-one |
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Traditional Name | (1'S,2S,4'R,5R,6S,8'S,10'E,12'S,13'R,14'E,16'E,20'R,21'S,24'R)-6-ethyl-12',21',24'-trihydroxy-11'-(hydroxymethyl)-5,13',22'-trimethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-2'-one |
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CAS Registry Number | Not Available |
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SMILES | CC[C@@H]1O[C@@]2(CC[C@H]1C)C[C@H]1C[C@H](C\C=C(CO)\[C@@H](O)[C@H](C)\C=C\C=C3/CO[C@@H]4[C@@H](O)C(C)=C[C@H](C(=O)O1)[C@@]34O)O2 |
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InChI Identifier | InChI=1S/C32H46O9/c1-5-26-18(2)11-12-31(41-26)15-24-14-23(40-31)10-9-21(16-33)27(34)19(3)7-6-8-22-17-38-29-28(35)20(4)13-25(30(36)39-24)32(22,29)37/h6-9,13,18-19,23-29,33-35,37H,5,10-12,14-17H2,1-4H3/b7-6+,21-9+,22-8+/t18-,19-,23+,24-,25-,26+,27+,28+,29-,31+,32+/m1/s1 |
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InChI Key | QNRGVUGZBUINDR-ZZAIWYOXSA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 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
- Oxane
- Tetrahydrofuran
- Tertiary alcohol
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Acetal
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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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