Lenoremycin sodium
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| Category | Antibiotics |
| Catalog number | BBF-03029 |
| CAS | 58399-44-3 |
| Molecular Weight | 873.10 |
| Molecular Formula | C47H77NaO13 |
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Description
It is a polyether antibiotic produced by the strain of Streptomyces hygroscopicus A-130. It has the effect of anti-gram-positive bacteria, mycobacterium and protozoa, and can be used as a feed additive to control Eimeriatenella infection.
Specification
| Related CAS | 51257-84-2 (free acid) |
| Synonyms | Antibiotic A130 sodium salt; Dianemycin, 10-demethyl-19-de((tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl)oxy)-12-methyl-11-O-(tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl)-, monosodium salt, (11(2R,5S,6R),12R)-; Antibiotic A-130A Sodium salt |
| IUPAC Name | sodium;(E,2S,4R,8S)-8-[(2S,5R,6R,7R,9S)-2-[(2R,4S,6R,9R)-2-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-4,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-7-[(2R,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-2,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4,6-trimethyl-5-oxonon-6-enoate |
| Canonical SMILES | CC1CCC(OC12C(CC(O2)C3C(CC(C(O3)(CO)O)C)C)C)C4(CCC5(O4)C(C(CC(O5)C(C)C=C(C)C(=O)C(C)CC(C)C(=O)[O-])OC6CCC(C(O6)C)OC)C)C.[Na+] |
| InChI | InChI=1S/C47H78O13.Na/c1-25(19-26(2)41(49)27(3)20-29(5)43(50)51)36-23-37(55-40-16-14-35(53-12)34(10)54-40)33(9)46(56-36)18-17-44(11,60-46)39-15-13-30(6)47(58-39)32(8)22-38(57-47)42-28(4)21-31(7)45(52,24-48)59-42;/h19,25,27-40,42,48,52H,13-18,20-24H2,1-12H3,(H,50,51);/q;+1/p-1/b26-19+;/t25-,27+,28-,29-,30+,31+,32-,33+,34+,35-,36-,37+,38+,39+,40-,42-,44-,45-,46+,47?;/m0./s1 |
| InChI Key | SLTQRBSNSQCBNO-GZEIRFRYSA-M |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycobacteria; Parasites |
| Melting Point | 227-231°C |
| Solubility | Soluble in Ethanol, Chloroform |
Reference Reading
1. Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6
Khaled A Shaaban, Meredith A Saunders, Yinan Zhang, Tuan Tran, Sherif I Elshahawi, Larissa V Ponomareva, Xiachang Wang, Jianjun Zhang, Gregory C Copley, Manjula Sunkara, Madan K Kharel, Andrew J Morris, James C Hower, Matthew S Tremblay, Mark A Prendergast, Jon S Thorson J Nat Prod. 2017 Jan 27;80(1):2-11. doi: 10.1021/acs.jnatprod.6b00948. Epub 2016 Dec 28.
The isolation and structure elucidation of six new bacterial metabolites [spoxazomicin D (2), oxachelins B and C (4, 5), and carboxamides 6-8] and 11 previously reported bacterial metabolites (1, 3, 9-12a, and 14-18) from Streptomyces sp. RM-14-6 is reported. Structures were elucidated on the basis of comprehensive 1D and 2D NMR and mass spectrometry data analysis, along with direct comparison to synthetic standards for 2, 11, and 12a,b. Complete 2D NMR assignments for the known metabolites lenoremycin (9) and lenoremycin sodium salt (10) were also provided for the first time. Comparative analysis also provided the basis for structural revision of several previously reported putative aziridine-containing compounds [exemplified by madurastatins A1, B1, C1 (also known as MBJ-0034), and MBJ-0035] as phenol-dihydrooxazoles. Bioactivity analysis [including antibacterial, antifungal, cancer cell line cytotoxicity, unfolded protein response (UPR) modulation, and EtOH damage neuroprotection] revealed 2 and 5 as potent neuroprotectives and lenoremycin (9) and its sodium salt (10) as potent UPR modulators, highlighting new functions for phenol-oxazolines/salicylates and polyether pharmacophores.
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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 ╳
