Neoenactin A
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| Category | Antibiotics |
| Catalog number | BBF-02113 |
| CAS | 88231-85-0 |
| Molecular Weight | 372.50 |
| Molecular Formula | C19H36N2O5 |
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Description
Neoenactin A is originally isolated from Streptoverticillium olivoreticuli subsp. neoenacticus. It has strong anti-yeastlike and filamentous fungal effects.
Specification
| Synonyms | Propanamide,2-amino-N-(3,10-dioxohexadecyl)-N,3-dihydroxy-, (S)- |
| IUPAC Name | (2S)-2-amino-N-(3,10-dioxohexadecyl)-N,3-dihydroxypropanamide |
| Canonical SMILES | CCCCCCC(=O)CCCCCCC(=O)CCN(C(=O)C(CO)N)O |
| InChI | InChI=1S/C19H36N2O5/c1-2-3-4-7-10-16(23)11-8-5-6-9-12-17(24)13-14-21(26)19(25)18(20)15-22/h18,22,26H,2-15,20H2,1H3/t18-/m0/s1 |
| InChI Key | RBILPDRITRQXOM-SFHVURJKSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 144-145°C |
Reference Reading
1. A new group of antibiotics, hydroxamic acid antimycotic antibiotics. II. The structure of neoenactins NL1 and NL2 and structure-activity relationship
H Okada, K Yamamoto, S Tsutano, Y Inouye, S Nakamura, J Furukawa J Antibiot (Tokyo). 1989 Feb;42(2):276-82. doi: 10.7164/antibiotics.42.276.
The structures of neoenactins (NEs) NL1 and NL2, novel antimycotic antibiotics produced by Streptoverticillium olivoreticuli in a precursor-oriented fashion, were elucidated by 1H and 13C NMR and mass spectroscopic studies. The structures of both antibiotics are closely related to that of NE-A, the major component of NE congeners, being classified in the group of hydroxamic acid antimycotic antibiotics in which L-serine and a diketo amine form a hydroxamic acid structure. To study the role of the carbonyl groups in the biological activities of the hydroxamic acid antimycotic antibiotics, NE-A was modified by reaction with various carbonyl reagents. In terms of antimycotic activity, the derivatives are classified into two distinct groups; the first ones are fairly comparable to but not exceeding and the second ones are less active than NE-A depending on their tendency to revert to NE-A by hydrolysis. In general, the biological activities of the derivatives are inversely proportional to their stabilities to hydrolysis.
2. A new group of antibiotics, hydroxamic acid antimycotic antibiotics. I. Precursor-initiated changes in productivity and biosynthesis of neoenactins NL1 and NL2
H Okada, K Yamamoto, S Tsutano, S Nakamura J Antibiot (Tokyo). 1988 Jul;41(7):869-74. doi: 10.7164/antibiotics.41.869.
Neoenactins (NEs) are L-serine-containing antifungal antibiotics produced by Streptoverticillium olivoreticuli. The effect of supplementation of individual amino acids on the production of NEs by this organism was examined from both quantitative and qualitative view points by using a nitrogen source-restricted medium. L-Alanine, L-arginine, L-glutamine, L-histidine, L-lysine and L-proline increased significantly the total productivity of NEs without changing the production ratio of the congeners. The supplementation of L-norvaline, L-isoleucine, L-leucine and L-valine to the culture medium resulted in selective enhancement of the production of NEs A, B1, B2, and M1, respectively, while significant change was not observed in terms of overall production of NEs. When L-norleucine was employed as an amino acid supplement, new NE congeners, named NEs NL1 and NL2, were preferentially produced; but the amount of NEs produced was not markedly affected.
3. Computational Investigations on the Natural Small Molecule as an Inhibitor of Programmed Death Ligand 1 for Cancer Immunotherapy
Geethu S Kumar, Mahmoud Moustafa, Amaresh Kumar Sahoo, Petr Malý, Shiv Bharadwaj Life (Basel). 2022 Apr 29;12(5):659. doi: 10.3390/life12050659.
Several therapeutic monoclonal antibodies approved by the FDA are available against the PD-1/PD-L1 (programmed death 1/programmed death ligand 1) immune checkpoint axis, which has been an unprecedented success in cancer treatment. However, existing therapeutics against PD-L1, including small molecule inhibitors, have certain drawbacks such as high cost and drug resistance that challenge the currently available anti-PD-L1 therapy. Therefore, this study presents the screening of 32,552 compounds from the Natural Product Atlas database against PD-L1, including three steps of structure-based virtual screening followed by binding free energy to refine the ideal conformation of potent PD-L1 inhibitors. Subsequently, five natural compounds, i.e., Neoenactin B1, Actinofuranone I, Cosmosporin, Ganocapenoid A, and 3-[3-hydroxy-4-(3-methylbut-2-enyl)phenyl]-5-(4-hydroxybenzyl)-4-methyldihydrofuran-2(3H)-one, were collected based on the ADMET (absorption, distribution, metabolism, excretion, and toxicity) profiling and binding free energy (>-60 kcal/mol) for further computational investigation in comparison to co-crystallized ligand, i.e., JQT inhibitor. Based on interaction mapping, explicit 100 ns molecular dynamics simulation, and end-point binding free energy calculations, the selected natural compounds were marked for substantial stability with PD-L1 via intermolecular interactions (hydrogen and hydrophobic) with essential residues in comparison to the JQT inhibitor. Collectively, the calculated results advocate the selected natural compounds as the putative potent inhibitors of PD-L1 and, therefore, can be considered for further development of PD-L1 immune checkpoint inhibitors in cancer immunotherapy.
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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 ╳
