Dactylocycline B
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| Category | Bioactive by-products |
| Catalog number | BBF-00781 |
| CAS | 125622-13-1 |
| Molecular Weight | 712.10 |
| Molecular Formula | C31H38ClN3O14 |
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Description
Dactylocycline is a tetracycline antibiotic produced by Dactylospoangium sp.. Dactylocycline B has anti-Gram-positive bacteria and weak anti-Gram-negative bacteria activity, and is not cross-resistant with tetracycline-resistant bacteria.
Specification
| Synonyms | 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,4a,10,12,12a-pentahydroxy-8-methoxy-6-methyl-1,11-dioxo-6-((2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-alpha-L-arabino-hexopyranosyl)oxy)-, (4R-(4alpha,4aalpha,5aalpha,6alpha,12aalpha))-; 7-chloro-4-(dimethylamino)-3,4a,10,12,12a-pentahydroxy-8-methoxy-6-((5-methoxy-4,6-dimethyl-4-nitrotetrahydro-2H-pyran-2-yl)oxy)-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide |
| Storage | Store at -20°C |
| IUPAC Name | 7-chloro-4-(dimethylamino)-1,4a,10,11,12a-pentahydroxy-8-methoxy-6-(5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl)oxy-6-methyl-3,12-dioxo-5,5a-dihydro-4H-tetracene-2-carboxamide |
| Canonical SMILES | CC1C(C(CC(O1)OC2(C3CC4(C(C(=O)C(=C(C4(C(=O)C3=C(C5=C2C(=C(C=C5O)OC)Cl)O)O)O)C(=O)N)N(C)C)O)C)(C)[N+](=O)[O-])OC |
| InChI | InChI=1S/C31H38ClN3O14/c1-11-26(47-7)28(2,35(44)45)10-15(48-11)49-29(3)12-9-30(42)23(34(4)5)22(38)18(27(33)41)25(40)31(30,43)24(39)16(12)21(37)17-13(36)8-14(46-6)20(32)19(17)29/h8,11-12,15,23,26,36-37,40,42-43H,9-10H2,1-7H3,(H2,33,41) |
| InChI Key | TZTDHPHRCVMDBT-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 843.3°C at 760 mmHg |
| Density | 1.6 g/cm3 |
| Solubility | Soluble in Methanol, DMSO, Water, Acetonitrile |
Reference Reading
1. Dactylocyclines, novel tetracycline derivatives produced by a Dactylosporangium sp. III. Absolute stereochemistry of the dactylocyclines
P V Devasthale, L A Mitscher, H Telikepalli, D Vander Velde, J Y Zou, H A Ax, A A Tymiak J Antibiot (Tokyo). 1992 Dec;45(12):1907-13. doi: 10.7164/antibiotics.45.1907.
The dactylocycline antibiotics were found through circular dichroism measurements, NMR spectroscopy and chemical transformations to possess the usual tetracycline family absolute configuration at carbons 4, 4a, 5a and 12a. The absolute stereochemistry about the C-6 carbon, however, was the reverse of that found with previously investigated tetracyclines.
2. Dactylocyclines, novel tetracycline derivatives produced by a Dactylosporangium sp. I. Taxonomy, production, isolation and biological activity
J S Wells, J O'Sullivan, C Aklonis, H A Ax, A A Tymiak, D R Kirsch, W H Trejo, P Principe J Antibiot (Tokyo). 1992 Dec;45(12):1892-8. doi: 10.7164/antibiotics.45.1892.
A screen for antibiotics with activity against tetracycline-resistant microorganisms has led to the isolation of Dactylosporangium sp. (ATCC 53693), a producer of several novel tetracycline derivatives. The major fermentation products, dactylocyclines A and B, were purified and MIC values determined against tetracycline-resistant and tetracycline-sensitive Gram-positive bacteria. The dactylocyclines represent the first naturally occurring tetracycline C2 amides which lack cross resistance with tetracycline.
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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 ╳
