Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 06:14:39 UTC |
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Updated at | 2022-09-12 06:14:40 UTC |
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NP-MRD ID | NP0325467 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 22'-ethyl-21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,6,11',13'-tetramethyl-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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Description | 22'-Ethyl-21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,6,11',13'-tetramethyl-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. 22'-ethyl-21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,6,11',13'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one is found in Streptomyces avermitilis. Based on a literature review very few articles have been published on 22'-ethyl-21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,6,11',13'-tetramethyl-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 | CCC1=CC2C(=O)OC3CC(CC=C(C)C(OC4CC(OC)C(OC5CC(OC)C(O)C(C)O5)C(C)O4)C(C)C=CC=C4COC(C1O)C24O)OC1(CCC(C)C(C)O1)C3 InChI=1S/C46H70O14/c1-10-30-18-34-44(49)56-33-19-32(60-45(22-33)17-16-24(2)27(5)59-45)15-14-26(4)41(25(3)12-11-13-31-23-53-43(40(30)48)46(31,34)50)57-38-21-36(52-9)42(29(7)55-38)58-37-20-35(51-8)39(47)28(6)54-37/h11-14,18,24-25,27-29,32-43,47-48,50H,10,15-17,19-23H2,1-9H3 |
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Synonyms | Not Available |
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Chemical Formula | C46H70O14 |
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Average Mass | 847.0520 Da |
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Monoisotopic Mass | 846.47656 Da |
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IUPAC Name | 22'-ethyl-21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,6,11',13'-tetramethyl-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 | 22'-ethyl-21',24'-dihydroxy-12'-({5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-4-methoxy-6-methyloxan-2-yl}oxy)-5,6,11',13'-tetramethyl-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 | CCC1=CC2C(=O)OC3CC(CC=C(C)C(OC4CC(OC)C(OC5CC(OC)C(O)C(C)O5)C(C)O4)C(C)C=CC=C4COC(C1O)C24O)OC1(CCC(C)C(C)O1)C3 |
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InChI Identifier | InChI=1S/C46H70O14/c1-10-30-18-34-44(49)56-33-19-32(60-45(22-33)17-16-24(2)27(5)59-45)15-14-26(4)41(25(3)12-11-13-31-23-53-43(40(30)48)46(31,34)50)57-38-21-36(52-9)42(29(7)55-38)58-37-20-35(51-8)39(47)28(6)54-37/h11-14,18,24-25,27-29,32-43,47-48,50H,10,15-17,19-23H2,1-9H3 |
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InChI Key | BCSHYJUZBCFRJQ-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 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
- O-glycosyl compound
- Glycosyl compound
- Disaccharide
- Ketal
- Oxane
- Tetrahydrofuran
- Tertiary alcohol
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Acetal
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- 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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