| Record Information |
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| Version | 2.0 |
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| Created at | 2021-01-06 04:53:23 UTC |
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| Updated at | 2021-07-15 17:30:44 UTC |
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| NP-MRD ID | NP0019350 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Virginiamycin M1 |
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| Provided By | NPAtlas |
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| Description | Virginiamycin m1 is also known as staphylomycin m or ostreogrycin g. Virginiamycin M1 is found in Streptomyces virginiae and Unknown-fungus sp.. Virginiamycin M1 was first documented in 1986 (PMID: 3084440). Based on a literature review a significant number of articles have been published on virginiamycin m1 (PMID: 34157539) (PMID: 34043498) (PMID: 33774675) (PMID: 32924591) (PMID: 32522108) (PMID: 31307989). |
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| Structure | [H]O[C@]1([H])\C([H])=C(/C(/[H])=C([H])\C([H])([H])N([H])C(=O)\C([H])=C([H])/[C@@]([H])(C([H])([H])[H])[C@]([H])(OC(=O)C2=C([H])C([H])([H])C([H])([H])N2C(=O)C2=C([H])OC(=N2)C([H])([H])C(=O)C1([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])\C([H])([H])[H] InChI=1S/C28H35N3O7/c1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b7-5-,10-9-,18-13-/t19-,20-,26-/m1/s1 |
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| Synonyms | | Value | Source |
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| Ostreogrycin g | MeSH | | Pristinamycin iia | MeSH | | Pristinamycin iib | MeSH | | Staphylomycin m | MeSH | | Staphylomycin m1 | MeSH | | Streptogramin a | MeSH | | Virginiamycin factor m1 | MeSH | | Virginiamycin iib | MeSH |
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| Chemical Formula | C28H35N3O7 |
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| Average Mass | 525.6020 Da |
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| Monoisotopic Mass | 525.24750 Da |
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| IUPAC Name | (10R,11R,12Z,17Z,19Z,21S)-21-hydroxy-11,19-dimethyl-10-(propan-2-yl)-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^{3,7}]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone |
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| Traditional Name | (10R,11R,12Z,17Z,19Z,21S)-21-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.0^{3,7}]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)C2=COC(CC(=O)C[C@H](O)\C=C(\C)/C=C\CNC(=O)\C=C/[C@H]1C)=N2 |
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| InChI Identifier | InChI=1S/C28H35N3O7/c1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b7-5-,10-9-,18-13-/t19-,20-,26-/m1/s1 |
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| InChI Key | DAIKHDNSXMZDCU-QHKJSJJMSA-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 |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Classification | Not classified |
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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 | - Burridge R, Warren C, Phillips I: Macrolide, lincosamide and streptogramin resistance in Campylobacter jejuni/coli. J Antimicrob Chemother. 1986 Mar;17(3):315-21. doi: 10.1093/jac/17.3.315. [PubMed:3084440 ]
- Ehrhart AL, Granek EF: Pharmaceuticals and alkylphenols in transplanted Pacific oysters (Crassostrea gigas): Spatial variation and growth effects. Mar Pollut Bull. 2021 Sep;170:112584. doi: 10.1016/j.marpolbul.2021.112584. Epub 2021 Jun 20. [PubMed:34157539 ]
- Gaugain M, Raynaud A, Bourcier S, Verdon E, Hurtaud-Pessel D: Development of a liquid chromatography-tandem mass spectrometry method to determine colistin, bacitracin and virginiamycin M1 at cross-contamination levels in animal feed. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2021 May 27:1-14. doi: 10.1080/19440049.2021.1922760. [PubMed:34043498 ]
- De Alwis HG, Nochetto C, Kijak PJ: An LC-MS/MS Method for the Determination of Antibiotic Residues in Distillers Grains: Collaborative Study. J AOAC Int. 2021 Mar 28. pii: 6198108. doi: 10.1093/jaoacint/qsab026. [PubMed:33774675 ]
- Jiang ZK, Hu XX, Xiao LL, Ren YR, Shakhtina AN, Lukianov DA, Osterman IA, Sergiev PV, Dontsova OA, Wang H, Wu G, You XF, Sun CH: Beilunmycin, a new virginiamycins antibiotic from mangrove-derived Streptomyces sp. 2BBP-J2 and the antibacterial activity by inhibiting protein translation. J Asian Nat Prod Res. 2020 Sep 14:1-9. doi: 10.1080/10286020.2020.1810669. [PubMed:32924591 ]
- Wu IL, Turnipseed SB, Andersen WC, Madson MR: Analysis of peptide antibiotic residues in milk using liquid chromatography-high resolution mass spectrometry (LC-HRMS). Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2020 Aug;37(8):1264-1278. doi: 10.1080/19440049.2020.1766703. Epub 2020 Jun 10. [PubMed:32522108 ]
- Garcia-Martin AB, Schwendener S, Perreten V: The tva(A) Gene from Brachyspira hyodysenteriae Confers Decreased Susceptibility to Pleuromutilins and Streptogramin A in Escherichia coli. Antimicrob Agents Chemother. 2019 Aug 23;63(9). pii: AAC.00930-19. doi: 10.1128/AAC.00930-19. Print 2019 Sep. [PubMed:31307989 ]
- Song X, Huang Q, Zhang Y, Zhang M, Xie J, He L: Rapid multiresidue analysis of authorized/banned cyclopolypeptide antibiotics in feed by liquid chromatography-tandem mass spectrometry based on dispersive solid-phase extraction. J Pharm Biomed Anal. 2019 Jun 5;170:234-242. doi: 10.1016/j.jpba.2019.03.050. Epub 2019 Mar 26. [PubMed:30939416 ]
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