Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 12:47:38 UTC |
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Updated at | 2022-09-11 12:47:38 UTC |
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NP-MRD ID | NP0314610 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s,6s,8s,9r,12z,14z,16r,25r,27s)-16-ethyl-3,6,8,9-tetrahydroxy-12-(methoxymethyl)-25,27-dimethyl-2-propyl-1-oxa-4-azacyclooctacosa-3,12,14-triene-20,28-dione |
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Description | Myxovirescin A belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (2s,6s,8s,9r,12z,14z,16r,25r,27s)-16-ethyl-3,6,8,9-tetrahydroxy-12-(methoxymethyl)-25,27-dimethyl-2-propyl-1-oxa-4-azacyclooctacosa-3,12,14-triene-20,28-dione is found in Myxococcus xanthus. It was first documented in 2003 (PMID: 12923079). Based on a literature review a significant number of articles have been published on Myxovirescin A (PMID: 32057784) (PMID: 31600864) (PMID: 31600444) (PMID: 17583882) (PMID: 17330904) (PMID: 16835859). |
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Structure | CCC[C@@H]1OC(=O)[C@@H](C)C[C@H](C)CCCCC(=O)CCC[C@@H](CC)\C=C/C=C(COC)/CC[C@@H](O)[C@@H](O)C[C@H](O)CN=C1O InChI=1S/C35H61NO8/c1-6-12-33-34(41)36-23-30(38)22-32(40)31(39)20-19-28(24-43-5)16-10-14-27(7-2)15-11-18-29(37)17-9-8-13-25(3)21-26(4)35(42)44-33/h10,14,16,25-27,30-33,38-40H,6-9,11-13,15,17-24H2,1-5H3,(H,36,41)/b14-10-,28-16-/t25-,26+,27+,30+,31-,32+,33+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C35H61NO8 |
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Average Mass | 623.8720 Da |
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Monoisotopic Mass | 623.43972 Da |
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IUPAC Name | (2S,6S,8S,9R,12Z,14Z,16R,25R,27S)-16-ethyl-3,6,8,9-tetrahydroxy-12-(methoxymethyl)-25,27-dimethyl-2-propyl-1-oxa-4-azacyclooctacosa-3,12,14-triene-20,28-dione |
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Traditional Name | (2S,6S,8S,9R,12Z,14Z,16R,25R,27S)-16-ethyl-3,6,8,9-tetrahydroxy-12-(methoxymethyl)-25,27-dimethyl-2-propyl-1-oxa-4-azacyclooctacosa-3,12,14-triene-20,28-dione |
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CAS Registry Number | Not Available |
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SMILES | CCC[C@@H]1OC(=O)[C@@H](C)C[C@H](C)CCCCC(=O)CCC[C@@H](CC)\C=C/C=C(COC)/CC[C@@H](O)[C@@H](O)C[C@H](O)CN=C1O |
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InChI Identifier | InChI=1S/C35H61NO8/c1-6-12-33-34(41)36-23-30(38)22-32(40)31(39)20-19-28(24-43-5)16-10-14-27(7-2)15-11-18-29(37)17-9-8-13-25(3)21-26(4)35(42)44-33/h10,14,16,25-27,30-33,38-40H,6-9,11-13,15,17-24H2,1-5H3,(H,36,41)/b14-10-,28-16-/t25-,26+,27+,30+,31-,32+,33+/m1/s1 |
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InChI Key | VQWNGCSUNKJFLW-ROEOKSPKSA-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 macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. |
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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 | Not Available |
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Direct Parent | Macrolides and analogues |
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Alternative Parents | |
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Substituents | - Macrolide
- Cyclic carboximidic acid
- Cyclic ketone
- Secondary alcohol
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Polyol
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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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General References | - Izzat S, Rachid S, Ajdidi A, El-Nakady YA, Liu XX, Ye BC, Muller R: The ROK like protein of Myxococcus xanthus DK1622 acts as a pleiotropic transcriptional regulator for secondary metabolism. J Biotechnol. 2020 Mar 10;311:25-34. doi: 10.1016/j.jbiotec.2020.02.005. Epub 2020 Feb 11. [PubMed:32057784 ]
- Wang C, Liu X, Zhang P, Wang Y, Li Z, Li X, Wang R, Shang Z, Yan J, He H, Wang J, Hu W, Li Y: Bacillus licheniformis escapes from Myxococcus xanthus predation by deactivating myxovirescin A through enzymatic glucosylation. Environ Microbiol. 2019 Dec;21(12):4755-4772. doi: 10.1111/1462-2920.14817. Epub 2019 Oct 28. [PubMed:31600864 ]
- Ellis BM, Fischer CN, Martin LB, Bachmann BO, McLean JA: Spatiochemically Profiling Microbial Interactions with Membrane Scaffolded Desorption Electrospray Ionization-Ion Mobility-Imaging Mass Spectrometry and Unsupervised Segmentation. Anal Chem. 2019 Nov 5;91(21):13703-13711. doi: 10.1021/acs.analchem.9b02992. Epub 2019 Oct 24. [PubMed:31600444 ]
- Simunovic V, Muller R: Mutational analysis of the myxovirescin biosynthetic gene cluster reveals novel insights into the functional elaboration of polyketide backbones. Chembiochem. 2007 Jul 23;8(11):1273-80. doi: 10.1002/cbic.200700153. [PubMed:17583882 ]
- Simunovic V, Muller R: 3-hydroxy-3-methylglutaryl-CoA-like synthases direct the formation of methyl and ethyl side groups in the biosynthesis of the antibiotic myxovirescin A. Chembiochem. 2007 Mar 26;8(5):497-500. doi: 10.1002/cbic.200700017. [PubMed:17330904 ]
- Simunovic V, Zapp J, Rachid S, Krug D, Meiser P, Muller R: Myxovirescin A biosynthesis is directed by hybrid polyketide synthases/nonribosomal peptide synthetase, 3-hydroxy-3-methylglutaryl-CoA synthases, and trans-acting acyltransferases. Chembiochem. 2006 Aug;7(8):1206-20. doi: 10.1002/cbic.200600075. [PubMed:16835859 ]
- Simunovic V, Gherardini FC, Shimkets LJ: Membrane localization of motility, signaling, and polyketide synthetase proteins in Myxococcus xanthus. J Bacteriol. 2003 Sep;185(17):5066-75. doi: 10.1128/JB.185.17.5066-5075.2003. [PubMed:12923079 ]
- LOTUS database [Link]
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