Lipomycin α
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| Category | Antibiotics |
| Catalog number | BBF-02654 |
| CAS | 51053-40-8 |
| Molecular Weight | 587.70 |
| Molecular Formula | C32H45NO9 |
| Purity | >95% by HPLC |
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Description
It is produced by the strain of Str. aureofaciens Tu117. It has strong activity of anti-gram-positive bacterial and no activity against fungi (including yeast).
Specification
| Synonyms | alpha-Lipomycin; 4-[13-[(2,6-Dideoxy-beta-D-ribo-hexopyranosyl)oxy]-10,12,14-trimethyl-1-oxopentadeca-2,4,6,8,10-pentenyl]-2,5-dihydro-3-hydroxy-1-methyl-5-oxo-1H-pyrrole-2-propanoic acid |
| Storage | Store at -20°C |
| IUPAC Name | 3-[(4E)-4-[(2E,4E,6E,8E,10E)-13-[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-10,12,14-trimethylpentadeca-2,4,6,8,10-pentaenylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid |
| Canonical SMILES | CC1C(C(CC(O1)OC(C(C)C)C(C)C=C(C)C=CC=CC=CC=CC(=C2C(=O)C(N(C2=O)C)CCC(=O)O)O)O)O |
| InChI | InChI=1S/C32H45NO9/c1-19(2)31(42-27-18-25(35)29(38)22(5)41-27)21(4)17-20(3)13-11-9-7-8-10-12-14-24(34)28-30(39)23(15-16-26(36)37)33(6)32(28)40/h7-14,17,19,21-23,25,27,29,31,34-35,38H,15-16,18H2,1-6H3,(H,36,37)/b9-7+,10-8+,13-11+,14-12+,20-17+,28-24+/t21?,22-,23?,25+,27+,29-,31?/m1/s1 |
| InChI Key | BRPRNHPFSOESDI-WTYFYQQMSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Orange-red Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 105°C |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Flexible docking-based molecular dynamics simulation of natural product compounds and Ebola virus Nucleocapsid (EBOV NP): a computational approach to discover new drug for combating Ebola
Erwin Prasetya Toepak, Ahmad Husein Alkaff, Mochammad Arfin Fardiansyah Nasution, Usman Sumo Friend Tambunan BMC Bioinformatics . 2018 Nov 20;19(Suppl 14):419. doi: 10.1186/s12859-018-2387-8.
Background:Ebola still remains as one of the most problematic infectious diseases in Africa with a high rate of mortality. Although this disease has been known for an almost half-century, there are no vaccines and drugs available in the market to treat Ebola. Zaire ebolavirus (EBOV), a single-stranded RNA virus which belongs to Filoviridae family and Mononegavirales order, is one of the virus causing Ebola. As one of seven proteins that EBOV encodes, Ebola virus nucleoprotein (EBOV NP) plays an imperative role in EBOV proliferation cycle. Therefore, the development of a new Ebola treatment can be targeted towards EBOV NP.Results:In this work, we screened about 190,084 natural product compounds from ZINC15 database through in silico virtual screening and flexible docking simulation. Furthermore, the bioavailability and toxicity prediction have been conducted as well. Two best ligands according to the simulation and prediction tests were progressed into the molecular dynamics simulation.Conclusion:In the end, we found that our proposed ligands, namely α-lipomycin (ZINC56874155) and 3-(((S)-1-amino-1,2,3,4-tetrahydroisoquinolin-5-yl)methyl)-5-((5-((5R,7S)-5,7-dihydroxy-3-oxodecyl)-2-hydroxyphenoxy) methyl)pyrrolo[3,4-b]pyrrol-5-ium (ZINC85628951), showed the promising results to be developed as a lead compounds for treating Ebola. Therefore, an experimental study is required to validate their inhibition activities against EBOV NP.
2. [Physicochemical properties and structure of the nonmacrolide polyene antibiotic altamycin A]
Iu D Shenin Antibiot Med Biotekhnol . 1986 Nov;31(11):835-41.
Altamycin A, an antibiotic described earlier was classified by its physicochemical and biological properties as belonging to the subgroup of polyenic nonmacrolides. Physicochemical properties of altamycin A and other representatives of nitrogen-containing polyenic nonmacrolides are presented. It is shown that the molecule of the antibiotic contains D-digitoxose (a sugar). The structure of the antibiotic aglycone was determined by the mass spectra of the oxidative degradation products of perhydroantibiotic, methyl heptahydroantibiotic and methyl permethylperhydroaglycone. Unlike alpha-lipomycin, altamycin A contains the tetraene system of conjugated methylene bonds.
3. Characterization and analysis of the regulatory network involved in control of lipomycin biosynthesis in Streptomyces aureofaciens Tü117
Victor Fedorenko, Bogdan Ostash, Liliya Horbal, Elisabeth Welle, Andriy Luzhetskyy, Tatsunosuke Nakamura, Maria Rabyk, Andreas Bechthold, Yuriy Rebets Appl Microbiol Biotechnol . 2010 Jan;85(4):1069-79. doi: 10.1007/s00253-009-2108-3.
Analysis of the alpha-lipomycin biosynthesis gene cluster of Streptomyces aureofaciens Tü117 led to the identification of five putative regulatory genes, which are congregated into a subcluster. Analysis of the lipReg1-4 and lipX1 showed that they encode components of two-component signal transduction systems (LipReg1 and LipReg2), multiple antibiotics resistance-type regulator (LipReg3), large ATP-binding regulators of the LuxR family-type regulator (LipReg4), and small ribonuclease (LipRegX1), respectively. A combination of targeted gene disruptions, complementation experiments, lipomycin production studies, and gene expression analysis via RT-PCR suggests that all regulatory lip genes are involved in alpha-lipomycin production. On the basis of the obtained data, we propose that LipReg2 controls the activity of LipReg1, which in its turn govern the expression of the alpha-lipomycin pathway-specific regulatory gene lipReg4. The ribonuclease gene lipX1 and the transporter regulator lipReg3 appear to work independently of genes lipReg1, lipReg2, and lipReg4.
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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 ╳
