Decatromicin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00794 |
| CAS | |
| Molecular Weight | 821.39 |
| Molecular Formula | C45H57ClN2O10 |
Online Inquiry
Description
Decatromicin A is an antibiotic produced by Actinomadura sp. MK73-NF4. Decatromicin A has anti-gram-positive bacteria activity.
Specification
| IUPAC Name | (1S,3S,6S,7E,10E,13R,16S,17S,18S,21R,22R)-17-[(2R,4R,5S,6R)-5-[(3-chloro-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=CN7)Cl)O)C)CC)O)C(=O)O3 |
| InChI | InChI=1S/C45H57ClN2O10/c1-7-26-21-45-39(51)34(42(55)58-45)38(50)44(8-2)27(12-10-9-11-23(3)20-43(45,6)22-29(26)41(53)54)14-15-28-30(44)16-13-24(4)37(28)57-33-19-32(49)35(25(5)56-33)48-40(52)36-31(46)17-18-47-36/h9-10,14-15,17-18,20,22,24-28,30,32-33,35,37,47,49-50H,7-8,11-13,16,19,21H2,1-6H3,(H,48,52)(H,53,54)/b10-9+,23-20+,38-34?/t24-,25+,26-,27+,28-,30+,32+,33-,35+,37-,43-,44+,45+/m0/s1 |
| InChI Key | LSANQCYQTPFAGU-PRRJNIGWSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 223-225°C |
Reference Reading
1. Secondary Metabolites of Actinomycetales as Potent Quorum Sensing Inhibitors Targeting Gram-Positive Pathogens: In Vitro and In Silico Study
Said E Desouky, Mohammed Abu-Elghait, Eman A Fayed, Samy Selim, Basit Yousuf, Yasuhiro Igarashi, Basel A Abdel-Wahab, Amnah Mohammed Alsuhaibani, Kenji Sonomoto, Jiro Nakayama Metabolites. 2022 Mar 15;12(3):246. doi: 10.3390/metabo12030246.
Anti-virulence agents are non-bacteriostatic and non-bactericidal emerging therapeutic options which hamper the production of virulence factors in pathogenic flora. In Staphylococcus aureus and Enterococcus faecalis, regulation of virulence genes' expression occurs through the cyclic peptide-mediated accessory gene regulator (agr) and its ortholog fsr quorum sensing systems, respectively. In the present study, we screened a set of 54 actinomycetales secondary metabolites as novel anti-virulence compounds targeting quorum sensing system of the Gram-positive bacteria. The results indicated that four compounds, Phenalinolactones A-D, BU-4664LMe, 4,5-dehydrogeldamycin, and Questinomycin A, potentially inhibit the agr quorum sensing system and hemolytic activity of S. aureus. On the other hand, Decatromicin A and B, Okilactomycin, Rishirilide A, Abyssomicin I, and Rebeccamycin selectively blocked the fsr quorum sensing system and the gelatinase production in E. faecalis at sub-lethal concentrations. Interestingly, Synerazol uniquely showed the capability to inhibit both fsr and agr quorum sensing systems. Further, in silico molecular docking studies were performed which provided closer insights into the mode of action of these compounds and proposed that the inhibitory activity of these compounds could be attributed to their potential ability to bind to the ATP-active site of S. aureus AgrA. Taken together, our study highlights the potential of actinomycetales secondary metabolites with diverse structures as anti-virulence quorum sensing inhibitors.
2. Decatromicins A and B, new antibiotics produced by Actinomadura sp. MK73-NF4. I. Taxonomy, isolation, physico-chemical properties and biological activities
I Momose, H Iinuma, N Kinoshita, Y Momose, S Kunimoto, M Hamada, T Takeuchi 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).
Recommended Products
| BBF-02614 | Nystatin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
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 ╳
