Heneicomycin
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| Category | Antibiotics |
| Catalog number | BBF-01338 |
| CAS | 66170-37-4 |
| Molecular Weight | 794.98 |
| Molecular Formula | C44H62N2O11 |
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Description
It is produced by the strain of Streptomyces filipinensis MA-4581 (NRRL 11044). It has anti-gram-positive bacteria, negative bacteria and mycoplasma activities, and has the effect of promoting animal growth.
Specification
| Synonyms | 2H-Pyran-2-acetamide, N-((2E,4E,6S,7R)-7-((2S,3S,4R,5R)-5-((1E,3E,5E)-7-(1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrienyl)tetrahydro-3,4-dihydroxy-2-furanyl)-6-methoxy-5-methyl-2,4-octadienyl)-alpha-ethyltetrahydro-2,4-dihydroxy-5,5-dimethyl-6-((1E,3Z)-1,3-pentadienyl)-, (alphaS,2S,4S,6S)-; 30-Deoxy-1-methylmocimycin; Antibiotic A 21A |
| IUPAC Name | (2S)-2-[(2S,4S,6S)-2,4-dihydroxy-5,5-dimethyl-6-[(1E,3Z)-penta-1,3-dienyl]oxan-2-yl]-N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-[(1E,3E,5E)-7-(4-hydroxy-1-methyl-2-oxopyridin-3-yl)-6-methyl-7-oxohepta-1,3,5-trienyl]oxolan-2-yl]-6-methoxy-5-methylocta-2,4-dienyl]butanamide |
| Canonical SMILES | CCC(C(=O)NCC=CC=C(C)C(C(C)C1C(C(C(O1)C=CC=CC=C(C)C(=O)C2=C(C=CN(C2=O)C)O)O)O)OC)C3(CC(C(C(O3)C=CC=CC)(C)C)O)O |
| InChI | InChI=1S/C44H62N2O11/c1-10-12-14-22-34-43(6,7)33(48)26-44(54,57-34)30(11-2)41(52)45-24-18-17-20-28(4)39(55-9)29(5)40-38(51)37(50)32(56-40)21-16-13-15-19-27(3)36(49)35-31(47)23-25-46(8)42(35)53/h10,12-23,25,29-30,32-34,37-40,47-48,50-51,54H,11,24,26H2,1-9H3,(H,45,52)/b12-10-,15-13+,18-17+,21-16+,22-14+,27-19+,28-20+/t29-,30-,32-,33+,34+,37+,38+,39-,40+,44+/m1/s1 |
| InChI Key | VKGDSUWMXCVJEA-HYJCFLTESA-N |
Properties
| Appearance | Light Yellow Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Mycoplasma |
| Boiling Point | 927.5 °C at 760 mmHg |
| Density | 1.24 g/cm3 |
| Solubility | Soluble in Methanol, Ethanol, Acetone, Chloroform, Butanol |
Reference Reading
1. The structure of heneicomycin
R S Dewey, O D Hensens, A W Douglas, G Albers-Schönberg J Antibiot (Tokyo). 1991 Aug;44(8):838-43. doi: 10.7164/antibiotics.44.838.
The antibiotic heneicomycin (1), C44H62N2O11, was isolated from cultures of Streptomyces filipinensis as an amorphous yellow powder. Mass spectral and NMR analysis showed the compound to be a deoxy modification of aurodox (2), a member of the elfamycin antibiotic family. A marked change in mass spectral fragmentation compared to aurodox and 1H NMR couplings indicated the absence of the hydroxyl at position 30 of aurodox (position 3 of the tetrahydropyran).
2. Antibacterial activity of heneicomycin
B M Frost, M E Valiant, E L Dulaney J Antibiot (Tokyo). 1979 Jun;32(6):626-9. doi: 10.7164/antibiotics.32.626.
Heneicomycin is structurally similar to efrotomycin, mocimycin (kirromycin) and X-5108 (goldinomycin). Comparisons were limited because of the small supplies available. All antibiotics show the same in vitro antibacterial spectrum although some test cultures were less sensitive to efrotomycin. Heneicomycin compared favorably with efrotomycin when given subcutaneously or per os against infections with Moraxella bovis and Streptococcus pyogenes. The raid elimination of heneicomycin observed following oral administration may account for its poor activity against a Bordetella bronchiseptica infection where efrotomycin is effective. It appears more like X-5108 than efrotomycin biologically. The disaccharide on efrotomycin may account for the difference observed.
3. Bioconversion capacity of Streptomyces sp GE44282, a producer of the antibiotics heneicomycin and aurodox
F Marinelli, S Stella, N Montanini, F Le Monnier, L Cavaletti, E Selva J Ind Microbiol. 1995 Jul;15(1):49-54. doi: 10.1007/BF01570013.
Streptomyces sp GE44282 was isolated in the course of a screening program for novel antibiotics. It co-produces heneicomycin and aurodox, two kirromycin-type antibiotics, which differ by the presence of an hydroxyl group at the C30 position of aurodox. Heneicomycin is converted into aurodox both by growing and resting cells of Streptomyces sp GE44282 and by the producer of aurodox, Streptomyces goldiniensis ATCC 21386. This bioconversion of heneicomycin is substrate-specific and is not observed using the producer of heneicomycin, Streptomyces filippiniensis NRRL 11044. The three strains show very similar taxonomic characteristics. These results suggest that heneicomycin is a precursor of aurodox, the production of which depends on the bioconversion capability expressed by the strain.
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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 ╳
