Chlorothricin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00638 |
| CAS | 34707-92-1 |
| Molecular Weight | 955.48 |
| Molecular Formula | C50H63ClO16 |
| Purity | >99% by HPLC |
Online Inquiry
Description
Chlorothricin is produced by the strain of Streptomyces antibioticus Tu 99. Related to kijanimicin, saccharocarcins, tetrocarcins and versipelostatin. It inhibits cholesterol biosynthesis from mevalonate, and inhibits pyruvate carboxylases purified from rat liver, chicken liver and azotobacter vinelandii.
Specification
| Synonyms | (4S,4aS,6aR,11E,12aR,15R,16aS,21aR,21bR)-4-[[4-O-[3-O-(3-Chloro-6-methoxy-2-methylbenzoyl)-2,6-dideoxy-β-D-arabino-hexopyranosyl]-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy]-1,2,3,4,4a,6a,7,8,9,10,12a,15,16,21,21a,21b-hexadecahydro-22-hydroxy-15,21a-dimethyl-18,21-dioxo-18H-16a,19-metheno-16aH-benzo[e]naphtho[2,1-m][1,4]dioxacyclopentadecin-14-carboxylic Acid; [4S-(4R*,4aR*,6aS*,11E,12aS*,15S*,16aR*,21aS*,21bS*)]-4-[[4-O-[3-O-(3-Chloro-6-methoxy-2-methylbenzoyl)-2,6-dideoxy-β-D-arabino-hexopyranosyl]-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy]-1,2,3,4,4a,6a,7,8,9,10,12a,15,16,21,21a,21b-hexadecahydro-22-hydroxy-15,21a-dimethyl-18,21-dioxo-18H-16a,19-metheno-16aH-benzo[e]naphtho[2,1-m][1,4]dioxacyclopentadecin-14-carboxylic Acid |
| Storage | Store at -20°C |
| IUPAC Name | (1S,3R,6R,7E,13R,16S,17S,21R,22R)-17-[(2R,4R,5S,6R)-5-[(2S,4R,5R,6R)-4-(3-chloro-6-methoxy-2-methylbenzoyl)oxy-5-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-28-hydroxy-3,22-dimethyl-23,26-dioxo-24,27-dioxapentacyclo[23.2.1.01,6.013,22.016,21]octacosa-4,7,14,25(28)-tetraene-4-carboxylic acid |
| Canonical SMILES | CC1CC23C(C=CCCCCC4C=CC5C(C4(C(=O)OC(=C2O)C(=O)O3)C)CCCC5OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC(=O)C8=C(C=CC(=C8C)Cl)OC)O)C=C1C(=O)O |
| InChI | InChI=1S/C50H63ClO16/c1-24-23-50-29(20-31(24)45(55)56)13-10-8-7-9-12-28-16-17-30-32(49(28,5)48(59)66-43(44(50)54)47(58)67-50)14-11-15-35(30)63-38-21-34(52)42(27(4)62-38)65-39-22-37(41(53)26(3)61-39)64-46(57)40-25(2)33(51)18-19-36(40)60-6/h10,13,16-20,24,26-30,32,34-35,37-39,41-42,52-54H,7-9,11-12,14-15,21-23H2,1-6H3,(H,55,56)/b13-10+/t24-,26-,27-,28-,29-,30+,32-,34-,35+,37-,38+,39+,41-,42-,49-,50+/m1/s1 |
| InChI Key | WUXHQHDSSKBJFH-DELKKKATSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 1050.8±65.0°C (Predicted) |
| Melting Point | 207°C |
| Density | 1.39±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Genetic characterization of the chlorothricin gene cluster as a model for spirotetronate antibiotic biosynthesis
Lei Shao, Xu-Dong Qu, Gong-Li Tang, Xin-Ying Jia, Jian Tang, Qun-Fei Zhao, Wen Liu, Zhen-Hua Tian Chem Biol . 2006 Jun;13(6):575-85. doi: 10.1016/j.chembiol.2006.03.008.
The biosynthetic gene cluster for chlorothricin (CHL) was localized to a 122 kb contiguous DNA from Streptomyces antibioticus DSM 40725, and its involvement in CHL biosynthesis was confirmed by gene inactivation and complementation. Bioinformatic analysis of the sequenced 111.989 kb DNA region revealed 42 open reading frames, 35 of which were defined to constitute the CHL gene cluster. An assembly model for CHL biosynthesis from D-olivose, 2-methoxy-5-chloro-6-methylsalicyclic acid, and chlorothricolide building blocks was proposed. This work represents cloning of a gene cluster for spirotetronate antibiotic biosynthesis and sets the stage to investigate the unusual macrolide biosynthesis including tandem Diels-Alder cyclizations, Baeyer-Villiger oxidation, and incorporation of an enoylpyruvate unit.
2. Identification and characterization of deschloro-chlorothricin obtained from a large natural product library targeting aurora A kinase in multiple myeloma
Edmond Fleischer, Nadire Özenver, Thomas Efferth, Anette Klinger, Sara Abdelfatah Invest New Drugs . 2021 Apr;39(2):348-361. doi: 10.1007/s10637-020-01012-2.
Multiple myeloma (MM) is a devastating disease with low survival rates worldwide. The mean lifetime of patients may be extendable with new drug alternatives. Aurora A kinase (AURKA) is crucial in oncogenesis, because its overexpression or amplification may incline the development of various types of cancer, including MM. Therefore, inhibitors of AURKA are innovative and promising targets. Natural compounds always represented a valuable resource for anticancer drug development. In the present study, based on virtual drug screening of more than 48,000 natural compounds, the antibiotic deschloro-chlorotricin (DCCT) has been identified to bind to AURKA with even higher binding affinity (free bindung energy: -12.25 kcal/mol) than the known AURKA inhibitor, alisertib (free binding energy: -11.25 kcal/mol). The in silico studies have been verified in vitro by using microscale thermophoresis. DCCT inhibited MM cell lines (KMS-11, L-363, RPMI-8226, MOLP-8, OPM-2, NCI-H929) with IC50values in a range from 0.01 to 0.12 μM. Furthermore, DCCT downregulated AURKA protein expression, induced G2/M cell cycle arrest and disturbed the cellular microtubule network as determined by Western blotting, flow cytometry, and fluorescence microscopy. Thus, DCCT may be a promising lead structure for further derivatization and the development of specific AURKA inhibitors in MM therapy.
3. Biosynthesis of the macrolide antibiotic chlorothricin: basic building blocks
H Pape, R Holzbach, E F Kreutzer, C Chang, D Hook, H G Floss Biochemistry . 1978 Feb 7;17(3):556-60. doi: 10.1021/bi00596a029.
The biosynthesis of chlorothricin (I), a macrolide antibiotic isolated from Streptomyces antibioticus Tü 99, has been studied by feeding experiments with 14C- and 3H-labeled precursors. Acetate and propionate, but not methionine and mevalonate, were incorporated into the macrocylic aglycone of the antibiotic. Glucose and the various carbon atoms of tyrosine, except the carboxyl carbon, also contributed label to the aglycone. Glucose also seems to be a specific precursor of the 2-deoxyrhamnose moiety, probably via a process involving a hydrogen shift from C-4 to C-6 of the hexose. The substituted 6-methylsalicylic acid moiety seems to be derived from acetate and one O-methyl group provided by methionine; shikimic acid is not incorporated.
Recommended Products
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-03755 | Actinomycin D | 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 ╳
