Enamidonin
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| Category | Antibiotics |
| Catalog number | BBF-01223 |
| CAS | 162559-40-2 |
| Molecular Weight | 705.84 |
| Molecular Formula | C37H51N7O7 |
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Description
It is produced by the strain of Streptomyces sp. 91-75. It's a lipopeptide antibiotic. It inhibits EGF-dependent [3H] thymidine involvement in Balb/MK cells (IC50 is 10 μg/mL), and it can restore the deformed SRCTS-NRK form to the normal flat form (ED50 is 10 μg/mL). No antimicrobial activity.
Specification
| Synonyms | Antibiotic RK 75 |
| IUPAC Name | (2E,4E,9E)-N-[(E)-3-[[(5S)-5-benzyl-14,14-dimethyl-3,6,9,15-tetraoxo-1,4,7,10,13-pentazabicyclo[10.2.1]pentadecan-8-yl]methylamino]-3-oxoprop-1-enyl]-13-hydroxytetradeca-2,4,9-trienamide |
| Canonical SMILES | CC(CCC=CCCCC=CC=CC(=O)NC=CC(=O)NCC1C(=O)NCC2C(=O)N(CC(=O)NC(C(=O)N1)CC3=CC=CC=C3)C(N2)(C)C)O |
| InChI | InChI=1S/C37H51N7O7/c1-26(45)16-12-9-7-5-4-6-8-10-15-19-31(46)38-21-20-32(47)39-23-29-34(49)40-24-30-36(51)44(37(2,3)43-30)25-33(48)41-28(35(50)42-29)22-27-17-13-11-14-18-27/h7-11,13-15,17-21,26,28-30,43,45H,4-6,12,16,22-25H2,1-3H3,(H,38,46)(H,39,47)(H,40,49)(H,41,48)(H,42,50)/b9-7+,10-8+,19-15+,21-20+/t26?,28-,29?,30?/m0/s1 |
| InChI Key | HEQUMWPCRPDUAA-WTKBPMQGSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 180-220 °C (dec.) |
| Solubility | Soluble in Methanol |
Reference Reading
1. Antibacterial Cyclic Lipopeptide Enamidonins with an Enamide-Linked Acyl Chain from a Streptomyces Species
Sangkeun Son, Sung-Kyun Ko, Seung Min Kim, Eun Kim, Gil Soo Kim, Byeongsan Lee, In-Ja Ryoo, Won-Gon Kim, Jung-Sook Lee, Young-Soo Hong, Jae-Hyuk Jang, Jong Seog Ahn J Nat Prod. 2018 Nov 26;81(11):2462-2469. doi: 10.1021/acs.jnatprod.8b00497. Epub 2018 Oct 19.
Three cyclic lipopeptides, including one known (1) and two new (2 and 3) compounds, that possess the rare enamide linkage group were discovered from Streptomyces sp. KCB14A132, an actinobacterium isolated from a soil sample collected from Jeung Island, Korea. The NMR and MS-based characterization showed that they differed in the amino acid residues in the peptide backbone. Application of Marfey's analysis, GITC derivatization, and modified Mosher's method, as well as ECD measurements provided the absolute configurations of enamidonin (1) and those of new compounds enamidonins B and C (2 and 3). The two new enamidonin analogues were shown to exhibit antibacterial activity against Gram-positive bacteria including methicillin-resistant and quinolone-resistant Staphylococcus aureus. Furthermore, evaluation of the extraction conditions and a close inspection of the LC-MS chromatograms revealed that the N, N-acetonide unit of the enamidonin family was formed during the acetone extraction process. The chemically prepared deacetonide derivatives of enamidonins were found to lack antibacterial activity, demonstrating that the dimethylimidazolidinone residue is necessary for antibacterial activity.
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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 ╳
