Etheromycin
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| Category | Antibiotics |
| Catalog number | BBF-03016 |
| CAS | 59149-05-2 |
| Molecular Weight | 915.16 |
| Molecular Formula | C48H82O16 |
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Description
It is a polyether antibiotic produced by the strain of Streptomyces hygroscopicus F. D. 23604. It has anti-gram-positive bacteria, fungi and coccidiococci effects.
Specification
| Related CAS | 59202-85-6 (sodium salt) |
| Synonyms | Antibiotic 38295; CP-38295; Antibiotic T 40517; Septamycin, 5,15-didemethoxy-14-demethyl-5-hydroxy-27-methoxy-8,20-dimethyl-, (2S,3R,4R,5R,6S,7R,8S,27S)-; 2H-Pyran-2-acetic acid, tetrahydro-2,4-dihydroxy-6-[(1S)-1-[(2S,5R,7S,9R,10R)-9-methoxy-2,10-dimethyl-2-[(2S,2'R,5R,5'R)-octahydro-2-methyl-5'-[(2S,3S,4S,5R,6S)-tetrahydro-6-hydroxy-4-methoxy-3,5,6-trimethyl-2H-pyran-2-yl][2,2'-bifuran]-5-yl]-1,6-dioxaspiro[4.5]dec-7-yl]ethyl]-a,3,5-trimethyl-5-[[(2S,5S,6R)-tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl]oxy]-, (2R,3R,4R,5S,6R)- |
| IUPAC Name | 2-[(2S,4R,5R,6R)-4-hydroxy-6-[(1R)-1-[(7S,9R,10R)-2-[5-[5-[(3S,4S,5R,6S)-6-hydroxy-4-methoxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]-5-methyloxolan-2-yl]-9-methoxy-2,7,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]ethyl]-5-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-5-methyloxan-2-yl]propaneperoxoic acid |
| Canonical SMILES | CC1C(OC(C(C1OC)C)(C)O)C2CCC(O2)C3(CCC(O3)C4(CCC5(O4)C(C(CC(O5)(C)C(C)C6C(C(CC(O6)C(C)C(=O)OO)O)(C)OC7CCC(C(O7)C)OC)OC)C)C)C |
| InChI | InChI=1S/C48H82O16/c1-25(42(50)62-52)33-23-35(49)46(10,60-38-18-16-31(53-12)30(6)56-38)41(58-33)29(5)45(9)24-34(54-13)27(3)48(64-45)22-21-44(8,63-48)37-19-20-43(7,59-37)36-17-15-32(57-36)40-26(2)39(55-14)28(4)47(11,51)61-40/h25-41,49,51-52H,15-24H2,1-14H3/t25?,26-,27+,28+,29+,30+,31-,32?,33-,34+,35+,36?,37?,38-,39-,40?,41+,43?,44?,45-,46+,47-,48?/m0/s1 |
| InChI Key | IQVROGAJHRXENX-HXLMOCOFSA-N |
Properties
| Appearance | White Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi; Parasites |
| Boiling Point | 877.8°C at 760 mmHg |
| Melting Point | 135-138°C |
| Density | 1.22 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Studies on the ionophorous antibiotics. XXV. The assignments of the 13C-NMR spectra of dianemycin and lenoremycin
K Mizoue, H Seto, T Mizutani, M Yamagishi, A Kawashima, S Omura, M Ozeki, N Otake J Antibiot (Tokyo). 1980 Feb;33(2):144-56. doi: 10.7164/antibiotics.33.144.
All the resonances observed in the 13C-NMR spectra of polyether antibiotics, dianemycin and lenoremycin (Ro 21-6150) have been assigned by the aid of selective proton decoupling experiments, T1 value measurements and biosynthetic methods as well as comparison to model compounds such as monensin, nigericin, etheromycin and carriomycin.
2. Applications of fast atom bombardment mass spectrometry and fast atom bombardment mass spectrometry-mass spectrometry to the maduramicins and other polyether antibiotics
M M Siegel, W J McGahren, K B Tomer, T T Chang Biomed Environ Mass Spectrom. 1987 Jan;14(1):29-38. doi: 10.1002/bms.1200140108.
Fast atom bombardment mass spectrometry (FAB MS) and fast atom bombardment mass spectrometry-mass spectrometry (FAB MS/MS) were used to study the monovalent glycoside polyether antibiotics maduramicin alpha, beta and delta and the maduramicin alpha salts, their derivatives and degradation products. Also, representative compounds from three major classes of polyether antibiotics were studied: the monovalent polyethers, nigericin and monensin A, the divalent polyether lasalocid A and the monovalent glycoside polyethers septamycin, BL580 delta, etheromycin and carriomycin. The respective FAB fragment and decomposition ions were correlated with the known structures. The FAB spectra of all the polyethers contained metal-adduct molecular ions. Protonated molecular ions were absent. All the polyethers having a beta-hemiketal carboxylic acid group produced an abundant ion, often the base peak of the spectra, 62 daltons less than the corresponding metal-adduct molecular ion. The gas phase mechanism proposed for the formation of this fragment ion is an unusual unimolecular reaction which is initiated by an intramolecular proton transfer from the carboxylic acid to the hydroxy group of the beta-hemiketal, and, then followed by the concerted losses of water and carbon dioxide to produce the corresponding polyether olefin.
3. Synergistic effects in PR3+ transport mediated by ionophores across phosphatidylcholine vesicles
J Grandjean, P Laszlo Biochimie. 1989 Jan;71(1):183-6. doi: 10.1016/0300-9084(89)90149-1.
Use of a fluorescent probe for the intravesicular pH shows that synergisms previously observed in Pr3+ transport across phosphatidylcholine vesicles are explained by an increase in the proton counter-transport.
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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 ╳
