X-14873A
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| Category | Antibiotics |
| Catalog number | BBF-01668 |
| CAS | 88263-37-0 |
| Molecular Weight | 658.86 |
| Molecular Formula | C35H62O11 |
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Description
X-14873A is a polyether antibiotic produced by the fermentation of Streptomyces sp. X-14873. It is mainly active against Gram-positive bacteria.
Specification
| Synonyms | X 14873 A; X-14873 A; X14873 A; (5R)-4-Demethyl-4-ethyl-5-hydroxylysocellin |
| IUPAC Name | 2-[(2S,3R,4R,5S,6R)-3-ethyl-6-[(2S,3S,4S,6R)-6-[(2S,3S,5S)-5-[(2R,3R,5R)-5-ethyl-2-hydroxy-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-3,5-dimethyloxolan-2-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-5-methyloxan-2-yl]acetic acid |
| Canonical SMILES | CCC1C(C(C(OC1(CC(=O)O)O)C(C)C(C(C)C(=O)C(CC)C2C(CC(O2)(C)C3(C(CC(O3)(CC)C(CC)O)C)O)C)O)C)O |
| InChI | InChI=1S/C35H62O11/c1-11-23(30-18(5)15-32(10,44-30)35(43)19(6)16-33(14-4,46-35)25(36)13-3)28(40)20(7)27(39)21(8)31-22(9)29(41)24(12-2)34(42,45-31)17-26(37)38/h18-25,27,29-31,36,39,41-43H,11-17H2,1-10H3,(H,37,38)/t18-,19+,20-,21-,22-,23-,24+,25-,27+,29+,30-,31+,32-,33+,34-,35+/m0/s1 |
| InChI Key | RBJNZOJIUIUXJZ-SKTXWQMBSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 152°C |
Reference Reading
1. Susceptibility and resistance of ruminal bacteria to antimicrobial feed additives
T G Nagaraja, M B Taylor Appl Environ Microbiol. 1987 Jul;53(7):1620-5. doi: 10.1128/aem.53.7.1620-1625.1987.
Susceptibility and resistance of ruminal bacterial species to avoparcin, narasin, salinomycin, thiopeptin, tylosin, virginiamycin, and two new ionophore antibiotics, RO22-6924/004 and RO21-6447/009, were determined. Generally, antimicrobial compounds were inhibitory to gram-positive bacteria and those bacteria that have gram-positive-like cell wall structure. MICs ranged from 0.09 to 24.0 micrograms/ml. Gram-negative bacteria were resistant at the highest concentration tested (48.0 micrograms/ml). On the basis of their fermentation products, ruminal bacteria that produce lactic acid, butyric acid, formic acid, or hydrogen were susceptible and bacteria that produce succinic acid or ferment lactic acid were resistant to the antimicrobial compounds. Selenomonas ruminantium was the only major lactic acid-producing bacteria resistant to all the antimicrobial compounds tested. Avoparcin and tylosin appeared to be less inhibitory (MIC greater than 6.0 micrograms/ml) than the other compounds to the two major lactic acid-producing bacteria, Streptococcus bovis and Lactobacillus sp. Ionophore compounds seemed to be more inhibitory (MIC, 0.09 to 1.50 micrograms/ml) than nonionophore compounds (MIC, 0.75 to 12.0 micrograms/ml) to the major butyric acid-producing bacteria. Treponema bryantii, an anaerobic rumen spirochete, was less sensitive to virginiamycin than to the other antimicrobial compounds. Ionophore compounds were generally bacteriostatic, and nonionophore compounds were bactericidal. The specific growth rate of Bacteroides ruminicola was reduced by all the antimicrobial compounds except avoparcin. The antibacterial spectra of the feed additives were remarkably similar, and it appears that MICs may not be good indicators of the potency of the compounds in altering ruminal fermentation characteristics.
2. Three novel polyether antibiotics X-14889A, C, and D from a streptomycete. Taxonomy of the producing organism, fermentation production and biological properties of the antibiotics
C M Liu, J W Westley, J Chu, T E Hermann, M Liu, N Palleroni J Antibiot (Tokyo). 1993 Feb;46(2):275-9. doi: 10.7164/antibiotics.46.275.
Antibiotic X-14889A, C, and D are novel polyether antibiotics related to lysocellin and antibiotic X-14873A. They are produced by a streptomycete isolated from a soil of Wisconsin. The antibiotic X-14889C is active against Gram-positive bacteria and exhibits ionophore property.
3. Isolation and characterization of four polyether antibiotics, X-14889A, B, C, and D, closely related to lysocellin and the ferensimycins
J W Westley, C M Liu, J F Blount, L Todaro, L H Sello, N Troupe J Antibiot (Tokyo). 1993 Feb;46(2):280-6. doi: 10.7164/antibiotics.46.280.
Streptomyces sp. X-14889 (NRRL 15517) has been found to produce a number of novel polyether antibiotics and an orange pigment. One of the antibiotics, X-14889B (3) was identified as ferensimycin A, which in turn is an isomer of the well-studied polyether antibiotic, lysocellin (1). Of the three other antibiotics, X-14889C (4) is a lower homolog of ferensimycin A and antibiotics X-14889A (2) and D (5) which are respectively the descarboxy and anhydro-descarboxy forms of this same molecule. The latter compound, X-14889D is of interest as it contains an ether bridge across the terminal tetrahydrofuranyl ring in an analogous relationship to that reported earlier for antibiotics X-14873A (6) and G.
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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 ╳
