Decatromicin B
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| Category | Antibiotics |
| Catalog number | BBF-01697 |
| CAS | 235097-64-0 |
| Molecular Weight | 855.84 |
| Molecular Formula | C45H56Cl2N2O10 |
| Purity | >95% by HPLC |
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Description
Decatromicin B is an antibiotic produced by Actinomadura sp. MK73-NF4. Decatromicin B has anti-gram-positive bacteria activity.
Specification
| Storage | -20°C |
| IUPAC Name | (1S,3S,6S,7E,10E,13R,16S,17S,18S,21R,22R)-17-[(2R,4S,5S,6R)-5-[(3,5-dichloro-1H-pyrrole-2-carbonyl)amino]-4-hydroxy-6-methyloxan-2-yl]oxy-3,22-diethyl-23-hydroxy-6,8,18-trimethyl-25,27-dioxo-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-4,7,10,14,23-pentaene-4-carboxylic acid |
| Canonical SMILES | CCC1CC23C(=O)C(=C(C4(C5CCC(C(C5C=CC4CC=CCC(=CC2(C=C1C(=O)O)C)C)OC6CC(C(C(O6)C)NC(=O)C7=C(C=C(N7)Cl)Cl)O)C)CC)O)C(=O)O3 |
| InChI | InChI=1S/C45H56Cl2N2O10/c1-7-25-20-45-39(52)34(42(56)59-45)38(51)44(8-2)26(12-10-9-11-22(3)19-43(45,6)21-28(25)41(54)55)14-15-27-29(44)16-13-23(4)37(27)58-33-18-31(50)35(24(5)57-33)49-40(53)36-30(46)17-32(47)48-36/h9-10,14-15,17,19,21,23-27,29,31,33,35,37,48,50-51H,7-8,11-13,16,18,20H2,1-6H3,(H,49,53)(H,54,55)/b10-9+,22-19+,38-34?/t23-,24+,25-,26+,27-,29+,31-,33-,35+,37-,43-,44+,45+/m0/s1 |
| InChI Key | UYAXASMGHNZATD-FUUFVBDZSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 202-206°C |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. Decatromicins A and B, new antibiotics produced by Actinomadura sp. MK73-NF4. I. Taxonomy, isolation, physico-chemical properties and biological activities
Y Momose, M Hamada, H Iinuma, N Kinoshita, S Kunimoto, T Takeuchi, I Momose J Antibiot (Tokyo) . 1999 Sep;52(9):781-6. doi: 10.7164/antibiotics.52.781.
New antibiotics designated decatromicins A and B were isolated from the culture broth of Actinomadura sp. MK73-NF4. They were purified by butyl acetate extraction, silica gel column chromatography, silica gel TLC and Sephadex LH-20 column chromatography. Decatromicins A and B inhibited growth of Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA).
2. Antibacterial Spirotetronate Polyketides from an Actinomadura sp. Strain A30804
Yoganathan Kanagasundaram, Mario Wibowo, Lay-Kien Yang, Veronica W Ng, Siew-Bee Ng, Kuan-Chieh Ching, Chung-Yan Leong, Deborah C Seow, Zann Y Tan, Elaine J Chin Molecules . 2022 Nov 24;27(23):8196. doi: 10.3390/molecules27238196.
Large scale cultivation and chemical investigation of an extract obtained fromActimonadurasp. resulted in the identification of six previously undescribed spirotetronates (pyrrolosporin B and decatromicins C-G;7-12), along with six known congeners, namely decatromicins A-B (1-2), BE-45722B-D (3-5), and pyrrolosporin A (6). The chemical structures of compounds1-12were characterized via comparison with previously reported data and analysis of 1D/2D NMR and MS data. The structures of all new compounds were highly related to the spirotetronate type compounds, decatromicin and pyrrolosporin, with variations in the substituents on the pyrrole and aglycone moieties. All compounds were evaluated for antibacterial activity against the Gram-negative bacteria,Acinetobacter baumanniiand Gram-positive bacteria,Staphylococcus aureusand were investigated for their cytotoxicity against the human cancer cell line A549. Of these, decatromicin B (2), BE-45722B (3), and pyrrolosporin B (7) exhibited potent antibacterial activities against both Gram-positive (MIC90between 1-3 μM) and Gram-negative bacteria (MIC90values ranging from 12-36 μM) with weak or no cytotoxic activity against A549 cells.
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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 ╳
