Phenelfamycin A
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| Category | Antibiotics |
| Catalog number | BBF-02392 |
| CAS | 118498-91-2 |
| Molecular Weight | 938.11 |
| Molecular Formula | C51H71NO15 |
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Description
It is produced by the strain of Str. violaceoniger AB 9991-80, Str. violaceoniger AB 1047T-33. It has effect against anaerobic bacteria.
Specification
| IUPAC Name | (2E,4E,6E)-7-[(2S,3S,5R)-5-[(2S,3S,4E,6E)-8-[[(2S)-2-[(2R,3R,4R,6S)-2,4-dihydroxy-5,5-dimethyl-6-[(1E,3Z)-penta-1,3-dienyl]-3-(2-phenylacetyl)oxyoxan-2-yl]-3-[(2R,4S,5R,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxypropanoyl]amino]-3-methoxy-4-methylocta-4,6-dien-2-yl]-3-hydroxyoxolan-2-yl]hepta-2,4,6-trienoic acid |
| Canonical SMILES | CC=CC=CC1C(C(C(C(O1)(C(COC2CC(C(C(O2)C)O)OC)C(=O)NCC=CC=C(C)C(C(C)C3CC(C(O3)C=CC=CC=CC(=O)O)O)OC)O)OC(=O)CC4=CC=CC=C4)O)(C)C |
| InChI | InChI=1S/C51H71NO15/c1-9-10-14-25-41-50(5,6)47(58)48(66-43(56)28-35-22-15-13-16-23-35)51(60,67-41)36(31-63-44-30-40(61-7)45(57)34(4)64-44)49(59)52-27-20-19-21-32(2)46(62-8)33(3)39-29-37(53)38(65-39)24-17-11-12-18-26-42(54)55/h9-26,33-34,36-41,44-48,53,57-58,60H,27-31H2,1-8H3,(H,52,59)(H,54,55)/b10-9-,12-11+,20-19+,24-17+,25-14+,26-18+,32-21+/t33-,34-,36+,37-,38-,39+,40-,41-,44+,45+,46+,47-,48+,51+/m0/s1 |
| InChI Key | DVKFMCYYYHARAG-YPSRDPPCSA-N |
Properties
| Appearance | Light Brown Powder |
| Boiling Point | 1033.2°C at 760 mmHg |
| Melting Point | 140°C |
| Density | 1.25 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Effects of elfamycins on elongation factor Tu from Escherichia coli and Staphylococcus aureus
C C Hall, J D Watkins, N H Georgopapadakou Antimicrob Agents Chemother. 1989 Mar;33(3):322-5. doi: 10.1128/AAC.33.3.322.
Six kirromycin analogs (elfamycins) were compared on the basis of their inhibition of Escherichia coli poly(U)-directed poly(Phe) synthesis and stimulation of elongation factor Tu (EF-Tu)-associated GTPase activity. The elfamycins tested were kirromycin, aurodox, efrotomycin, phenelfamycin A, unphenelfamycin, and L-681,217. The last three lack the pyridone ring present in the other elfamycins. All the elfamycins inhibited poly(U)-dependent poly(Phe) synthesis and stimulated EF-Tu-associated GTPase activity, suggesting that the pyridone ring is not essential for activity. The six elfamycins were also examined in a poly(U)-directed, poly(Phe)-synthesizing system derived from Staphylococcus aureus and had 50% inhibitory concentrations of greater than or equal to 1 mM. When S. aureus ribosomes and E. coli elongation factors were combined in a hybrid poly(Phe)-synthesizing system, aurodox produced essentially complete inhibition of poly(Phe) synthesis with a 50% inhibitory concentration of 0.13 microM. This suggests that the observed high MICs of kirromycin and its congeners in S. aureus reflect a kirromycin-resistant EF-Tu rather than permeability constraints.
2. Phenelfamycins, a novel complex of elfamycin-type antibiotics. III. Activity in vitro and in a hamster colitis model
R N Swanson, D J Hardy, N L Shipkowitz, C W Hanson, N R Ramer, L J Coen, P B Fernandes J Antibiot (Tokyo). 1989 Jan;42(1):94-101. doi: 10.7164/antibiotics.42.94.
Phenelfamycins A, B, C, E, F and unphenelfamycin make up a recently isolated group of elfamycin-type antibiotics. All of the phenelfamycins were active against Gram-positive anaerobes, including Clostridium difficile. Phenelfamycin A was also active in vitro against Neisseria gonorrhoeae and Streptococci. Phenelfamycin A was found to be effective in prolonging the survival of hamsters in an animal model of C. difficile enterocolitis. After oral administration of phenelfamycin A to hamsters, antibiotic was detected in the caecal contents but not in the blood.
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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 ╳
