Geninthiocin
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| Category | Bioactive by-products |
| Catalog number | BBF-01866 |
| CAS | 158792-27-9 |
| Molecular Weight | 1132.08 |
| Molecular Formula | C50H49N15O15S |
| Purity | >95% by HPLC |
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Description
A thiopeptide antibiotic isolated from a streptomyces sp.; a potent activator of the tipa gene; a bacterial transcription regulator involved in multidrug resistance; displays a 10-fold selectivity for bacteria over mammalian cells lines; closely related to siomycin, a recently discovered inhibitor of oncogenic transcription factor, foxm1.
Specification
| Synonyms | NSC676674; 14-Demethylberinamycin |
| Storage | -20°C |
| IUPAC Name | (17E)-N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-17-ethylidene-14-(1-hydroxyethyl)-27-(2-hydroxypropan-2-yl)-33-methyl-24,30,37,40-tetramethylidene-12,15,22,25,28,35,38-heptaoxo-19,32,42-trioxa-9-thia-3,13,16,23,26,29,36,39,44,45,46,47-dodecazahexacyclo[39.2.1.18,11.118,21.131,34.02,7]heptatetraconta-1(43),2(7),3,5,8(47),10,18(46),20,31(45),33,41(44)-undecaene-4-carboxamide |
| Canonical SMILES | CC=C1C2=NC(=CO2)C(=O)NC(=C)C(=O)NC(C(=O)NC(=C)C3=NC(=C(O3)C)C(=O)NC(=C)C(=O)NC(=C)C4=NC(=CO4)C5=C(C=CC(=N5)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C6=NC(=CS6)C(=O)NC(C(=O)N1)C(C)O)C(C)(C)O |
| InChI | InChI=1S/C50H49N15O15S/c1-12-27-48-61-30(16-79-48)41(72)54-21(5)39(70)65-35(50(10,11)77)45(76)57-23(7)47-64-33(25(9)80-47)44(75)55-20(4)38(69)56-22(6)46-60-29(15-78-46)34-26(49-62-31(17-81-49)42(73)63-32(24(8)66)43(74)59-27)13-14-28(58-34)40(71)53-19(3)37(68)52-18(2)36(51)67/h12-17,24,32,35,66,77H,2-7H2,1,8-11H3,(H2,51,67)(H,52,68)(H,53,71)(H,54,72)(H,55,75)(H,56,69)(H,57,76)(H,59,74)(H,63,73)(H,65,70)/b27-12+ |
| InChI Key | JNUIXQXFKIJDIV-KKMKTNMSSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White to Off-White Amorphous Powder |
| Melting Point | 270-275°C |
| Density | 1.54±0.1 g/cm3 |
| Solubility | Soluble in DMF or DMSO. Moderately soluble in methanol or ethanol. Poor water solubility. |
Reference Reading
1. Geninthiocins E and F, two new cyclic thiopeptides with antiviral activities from soil-derived Streptomyces sp. CPCC 200267 using OSMAC strategy
Jing Wang, Zhe Guo, Shan Cen, Yan Tang, Liyan Yu, Yuan Fang, Dewu Zhang, Jinglin Bai, Jing Su, Linzhuan Wu J Antibiot (Tokyo) . 2022 Nov 25. doi: 10.1038/s41429-022-00580-0.
On the basis of the one strain-many compounds (OSMAC) strategy, two new cyclic thiopeptides, geninthiocins E and F, together with four known geninthiocin derivatives, geninthiocins A, B, C, and val-geninthiocin were isolated from Streptomyces sp. CPCC 200267. Their structures and absolute configurations were elucidated by extensive spectroscopic analyses and Marfey's method. Geninthiocin E (1), val-geninthiocin (3), geninthiocin A (4), and geninthiocin B (5) exhibited significant anti-influenza A virus activities with the IC50values of 28.7, 15.3, 7.3, and 18.3 μM, respectively. Compounds 3 and 4 showed moderate antibacterial activities against Staphylococcus aureus.
2. Ala-geninthiocin, a new broad spectrum thiopeptide antibiotic, produced by a marine Streptomyces sp. ICN19
Samuel Gnana Prakash Vincent, Enge Sudarman, Joachim Wink, Appadurai Muthamil Iniyan, Rajaretinam Rajesh Kannan J Antibiot (Tokyo) . 2019 Feb;72(2):99-105. doi: 10.1038/s41429-018-0115-2.
Bioassay-guided screening of antibacterial compounds from the cultured marine Streptomyces sp. ICN19 provided Ala-geninthiocin (1), along with its known analogs geninthiocin (2) and Val-geninthiocin (3) and the indolocarbazole staurosporine (4). The structure of 1 was determined on the basis of 1D and 2D NMR spectra and ESI-HRMS. The absolute configurations of the amino acid residues were determined by enantioselective GC-MS analysis. Compound 1 exhibited potent activity against Gram-positive bacteria including Staphylococcus aureus, Bacillus subtilis, Mycobacterium smegmatis, and Micrococcus luteus, as well as cytotoxicity against A549 human lung carcinoma cells with an IC50value of 6 nM.
3. Microbial metabolites with tipA promoter inducing activity. II. Geninthiocin, a novel thiopeptide produced by Streptomyces sp. DD84
T Hidaka, H Seto, B S Yun, K Furihata J Antibiot (Tokyo) . 1994 Sep;47(9):969-75. doi: 10.7164/antibiotics.47.969.
Geninthiocin was isolated from the mycelium of Streptomyces sp. DD84 as a tipA promoter inducing substance. Based on various NMR studies, its structure was established as a thiopeptide with oxazole and thiazole moieties, and several unusual amino acids.
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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 ╳
