Streptovaricin B
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| Category | Antibiotics |
| Catalog number | BBF-03071 |
| CAS | 11031-82-6 |
| Molecular Weight | 811.87 |
| Molecular Formula | C42H53NO15 |
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Description
Streptovaricin B is a macrolide Ansa antibiotic produced by Str. spectabilis NRRL 2494. It has a broad-spectrum anti-bacterial effect, but its anti-gram-negative bacteria activity is weak.
Specification
| Synonyms | Streptovaricin complex, fraction b; Streptovaricinoic acid, 21-acetate |
| IUPAC Name | methyl (9Z,11R,12R,13R,14R,15R,16R,17R,18R,19R)-2,16-diacetyloxy-12,14,18,19,31-pentahydroxy-3,7,11,13,17,19,21,27-octamethyl-6,28-dioxo-23,25-dioxa-5-azatetracyclo[20.7.1.14,29.026,30]hentriaconta-1,3,7,9,20,22(30),26,29(31)-octaene-15-carboxylate |
| Canonical SMILES | CC1C=CC=C(C(=O)NC2=C(C(=C3C(=C2O)C(=O)C(=C4C3=C(C(=CC(C(C(C(C(C(C(C1O)C)O)C(=O)OC)OC(=O)C)C)O)(C)O)C)OCO4)C)OC(=O)C)C)C |
| InChI | InChI=1S/C42H53NO15/c1-17-13-12-14-18(2)40(51)43-30-20(4)37(57-24(8)44)26-27(34(30)49)33(48)22(6)36-28(26)35(55-16-56-36)19(3)15-42(10,53)39(50)23(7)38(58-25(9)45)29(41(52)54-11)32(47)21(5)31(17)46/h12-15,17,21,23,29,31-32,38-39,46-47,49-50,53H,16H2,1-11H3,(H,43,51)/b13-12-,18-14?,19-15?/t17-,21-,23+,29-,31-,32-,38-,39-,42-/m1/s1 |
| InChI Key | IGDMPTXQUGESNO-HVYWSWGMSA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | bacteria; Gram-negative bacteria |
| Boiling Point | 933.7±65.0°C at 760 mmHg |
| Melting Point | 187-189°C |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. A reinvestigation of the sites of transcription and translation of Euglena chloroplastic phenylalanyl-tRNA synthetase
J L Lesiewicz, D S Herson Arch Microbiol. 1975 Oct 27;105(2):117-21. doi: 10.1007/BF00447124.
An attempt was made to determine the sites of chloroplast phenylalanyl-tRNA synthetase transcription and translation. Inhibitors of bacterial RNA and protein synthesis were added to logarithmic and stationary phase cultures of Euglena gracilis wild-type B. Logarithmic phase cultures were sensitive to both types of inhibitors. In stationary phase cultures plastid synthetase was reduced by RNA but not by protein synthesis inhibitors. The effect of the antibiotics on the mitochondrial enzyme was also noted. Several possible explanations of these resuults are discussed.
2. DNA replication by a DNA-membrane complex extracted from Bacillus subtilis: site of initiation in vitro and initiation potential of subcomplexes
J Laffan, W Firshein J Bacteriol. 1987 Jun;169(6):2819-27. doi: 10.1128/jb.169.6.2819-2827.1987.
A DNA-membrane complex extracted from Bacillus subtilis was studied further as a model system for initiation of bacterial DNA replication in vitro. Of three subcomplexes purified from the crude complex by a combination of CsCl and sucrose gradient centrifugation, the synthetic capability of only one was inhibited significantly by streptovaricin, a known inhibitor of RNA primer formation. A selective enrichment in the level of this subcomplex was obtained by manipulating a thymine-requiring mutant. The synthetic capabilities of an enriched and nonenriched DNA-membrane complex were compared in the presence and absence of streptovaricin. Although the rate and extent of DNA synthesis per unit of protein were approximately the same in the absence of the antibiotic, there was a much greater inhibition of synthesis shown by the enriched complex in the presence of streptovaricin. Although the amount of DNA present in the putative initiation subcomplex was less than 0.3 to 0.4% of the total DNA present in the crude complex, such DNA, except for a few quantitative differences, was still representative of genomic DNA. Newly synthesized DNA hybridized to specific origin- and non-origin-derived restriction fragments of the B. subtilis genome. However, when an elongation inhibitor (ddCTP) was added, hybridization of such DNA to almost all of the nonorigin fragments disappeared or was reduced drastically, whereas origin region hybridization patterns remained strong. The highest level of hybridization in the origin region occurred with a BamHI (B7) restriction fragment of 5.6 kilobases that has been implicated by others as one site initiation in vivo (N. Ogasawara, M. Seiki, and H. Yoshikawa, Nature (London) 281:702-704, 1979; S. J. Seror-Laurent and G. Henckes, Proc. Natl. Acad. Sci. USA 82:3586-3590, 1985).
3. Multi-Step In Silico Discovery of Natural Drugs against COVID-19 Targeting Main Protease
Eslam B Elkaeed, Fadia S Youssef, Ibrahim H Eissa, Hazem Elkady, Aisha A Alsfouk, Mohamed L Ashour, Mahmoud A El Hassab, Sahar M Abou-Seri, Ahmed M Metwaly Int J Mol Sci. 2022 Jun 21;23(13):6912. doi: 10.3390/ijms23136912.
In continuation of our antecedent work against COVID-19, three natural compounds, namely, Luteoside C (130), Kahalalide E (184), and Streptovaricin B (278) were determined as the most promising SARS-CoV-2 main protease (Mpro) inhibitors among 310 naturally originated antiviral compounds. This was performed via a multi-step in silico method. At first, a molecular structure similarity study was done with PRD_002214, the co-crystallized ligand of Mpro (PDB ID: 6LU7), and favored thirty compounds. Subsequently, the fingerprint study performed with respect to PRD_002214 resulted in the election of sixteen compounds (7, 128, 130, 156, 157, 158, 180, 184, 203, 204, 210, 237, 264, 276, 277, and 278). Then, results of molecular docking versus Mpro PDB ID: 6LU7 favored eight compounds (128, 130, 156, 180, 184, 203, 204, and 278) based on their binding affinities. Then, in silico toxicity studies were performed for the promising compounds and revealed that all of them have good toxicity profiles. Finally, molecular dynamic (MD) simulation experiments were carried out for compounds 130, 184, and 278, which exhibited the best binding modes against Mpro. MD tests revealed that luteoside C (130) has the greatest potential to inhibit SARS-CoV-2 main protease.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
