Virustomycin A
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| Category | Antibiotics |
| Catalog number | BBF-04417 |
| CAS | 84777-85-5 |
| Molecular Weight | 886.08 |
| Molecular Formula | C48H71NO14 |
| Purity | ≥98% |
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Description
Virustomycin A is a 18-membered macrolide antibiotic originally isolated from Streptomyces sp. AM-2604. It is effective against infectious and plant pathogenic fungi. It is active against trichomonads and various RNA and DNA viruses.
Specification
| Synonyms | AM 2604A; Antibiotic AM 2604A; [2R-[2R*[1S*[2R*,4R*,5S*,6R*(E)],2R*,3S*],3S*,4E,6E,9R*,10S*,11S*,12R*,13R*,14E,16Z]]-2-[3-(11-Ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6,14,16-tetraen-2-yl)-2-hydroxy-1-methylbutyl]tetrahydro-2-hydroxy-5-methyl-6-(1-propenyl)-2H-pyran-4-yl Ester 4-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-4-oxo-2-butenoic Acid; 23-O-De(4-O-aminocarbonyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-23-O-[4-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-1,4-dioxo-2-butenyl]concanamycin A |
| Storage | Store at -20°C |
| IUPAC Name | [(2R,4R,5S,6R)-2-[(2S,3R,4S)-4-[(2R,3S,4E,6E,9R,10S,11S,12R,13R,14E,16Z)-11-ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6,14,16-tetraen-2-yl]-3-hydroxypentan-2-yl]-2-hydroxy-5-methyl-6-[(E)-prop-1-enyl]oxan-4-yl] (E)-4-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-4-oxobut-2-enoate |
| Canonical SMILES | CCC1C(C(CC(=CC=CC(C(OC(=O)C(=CC(=CC(C1O)C)C)OC)C(C)C(C(C)C2(CC(C(C(O2)C=CC)C)OC(=O)C=CC(=O)NC3=C(CCC3=O)O)O)O)OC)C)C)O |
| InChI | InChI=1S/C48H71NO14/c1-12-15-36-30(7)39(61-41(53)21-20-40(52)49-42-34(50)18-19-35(42)51)25-48(58,63-36)32(9)45(56)31(8)46-37(59-10)17-14-16-26(3)22-28(5)43(54)33(13-2)44(55)29(6)23-27(4)24-38(60-11)47(57)62-46/h12,14-17,20-21,23-24,28-33,36-37,39,43-46,50,54-56,58H,13,18-19,22,25H2,1-11H3,(H,49,52)/b15-12+,17-14+,21-20+,26-16+,27-23+,38-24-/t28-,29-,30-,31+,32+,33+,36-,37+,39-,43+,44-,45-,46-,48-/m1/s1 |
| InChI Key | YIKWIQAIKGWYCF-ACOKZJPPSA-N |
Properties
| Appearance | Yellow Solid |
| Antibiotic Activity Spectrum | Fungi; Parasites; Viruses |
| Boiling Point | 989.2°C at 760 mmHg |
| Melting Point | 204.5°C |
| Density | 1.22 g/cm3 |
| Solubility | Soluble in Acetone, Chloroform, Ethanol, Methanol; Insoluble in Water, Hexane |
Reference Reading
1. AM-2604 A, a new antiviral antibiotic produced by a strain of Streptomyces
A Nakagawa, K Otoguro, H Hashimoto, H Shimizu, Y Iwai, K Hinotozawa, S Omura J Antibiot (Tokyo) . 1982 Dec;35(12):1632-7. doi: 10.7164/antibiotics.35.1632.
A novel antibiotic, AM-2604 A was isolated from the fermentation broth of Streptomyces sp. AM-2604 by solvent extraction and silica gel column chromatography. The antibiotic is pale yellow needles possessing UV absorption maxima at 280 nm and 330 nm (sh). The antibiotic possesses weak activity against fungi and trichomonad and potent inhibitory activity against various RNA and DNA viruses in vitro.
2. Selective and potent in vitro antitrypanosomal activities of ten microbial metabolites
Miyuki Namatame, Kazuro Shiomi, Satoshi Omura, Toshiaki Furusawa, Rokuro Masuma, Aki Ishiyama, Aki Nishihara, Haruki Yamada, Kazuhiko Otoguro, Yoko Takahashi J Antibiot (Tokyo) . 2008 Jun;61(6):372-8. doi: 10.1038/ja.2008.52.
More than 400 compounds isolated from soil microorganisms, and catalogued in the antibiotic library of the Kitasato Institute for Life Sciences, were screened against African trypanosomes. Ten compounds were found to have selective and potent antitrypanosomal activity in vitro: aureothin, cellocidin, destomycin A, echinomycin, hedamycin, irumamycin, LL-Z 1272beta, O-methylnanaomycin A, venturicidin A and virustomycin A. Results of the in vitro assays using the GUTat 3.1 strain of Trypanosomal brucei brucei and the STIB900 strain of T. b. rhodesiense are presented. Cytotoxicity was determined using a human MRC-5 cell line. This is the first report of antitrypanosomal activities of the 10 microbial metabolites listed above.
3. Isolation and structural elucidation of new 18-membered macrolide antibiotics, viranamycins A and B
K Nagai, Y Hayakawa, K Furihata, K Takaku, H Seto J Antibiot (Tokyo) . 1991 Dec;44(12):1294-9. doi: 10.7164/antibiotics.44.1294.
Two cytotoxic antibiotics, designated viranamycins A and B, were isolated from the culture broth of Streptomyces sp. CH41. Their structures were elucidated as new 18-membered macrolides related to virustomycin A and concanamycin A from NMR spectral analysis. Viranamycins A and B inhibited the growth of P388 mouse leukemia and KB human squamous-cell-carcinoma cells.
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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 ╳
