for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
A54556A is an unusual depsipeptide isolated from|Streptomyces|sp., featuring a trienone side chain. It is potently active against Gram positive and Gram negative bacteria, including MRSA. A54556A was the original lead structure of the recently re-discovered acyldepsipeptide (ADEP) antibiotics that act by activating and disregulating Clp-family proteins. ADEPs are considered important leads in the development of new generations of antibiotics against resistant bacteria.
| Canonical Smiles | CC=CC=CC=CC(=O)NC(CC1=CC=CC=C1)C(=O)NC2COC(=O)C3CC(CN3C(=O)C(NC(=O)C(N(C(=O)C4CCCN4C2=O)C)C)C)C |
|---|---|
| IUPAC Name | (2E,4E,6E)-N-[(2S)-1-oxo-3-phenyl-1-[[(3S,7S,9R,13S,16S,19S)-9,13,16,17-tetramethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetrazatricyclo[17.3.0.07,11]docosan-3-yl]amino]propan-2-yl]octa-2,4,6-trienamide |
| InChIKey | ZGRSXMWWGUOTAO-VIEJTCJKSA-N |
| INCHI | 1S/C38H50N6O8/c1-6-7-8-9-13-18-32(45)40-28(21-27-15-11-10-12-16-27)34(47)41-29-23-52-38(51)31-20-24(2)22-44(31)35(48)25(3)39-33(46)26(4)42(5)37(50)30-17-14-19-43(30)36(29)49/h6-13,15-16,18,24-26,28-31H,14,17,19-23H2,1-5H3,(H,39,46)(H,40,45)(H,41,47)/b7-6+,9-8+,18-13+/t24-,25+,26+,28+,29+,30+,31+/m1/s1 |
| Isomeric SMILES | C/C=C/C=C/C=C/C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@H]2COC(=O)[C@@H]3C[C@H](CN3C(=O)[C@@H](NC(=O)[C@@H](N(C(=O)[C@@H]4CCCN4C2=O)C)C)C)C |
| PubChem CID | 24767779 |
| Molecular Weight | 718.84 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Peptidomimetics |
| Subclass | Depsipeptides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Cyclic depsipeptides |
| Alternative Parents | Phenylalanine and derivatives Macrolide lactams Alpha amino acid esters N-acyl-alpha amino acids and derivatives Macrolactams Alpha amino acid amides Amphetamines and derivatives N-acyl amines Tertiary carboxylic acid amides Pyrrolidines Secondary carboxylic acid amides Carboxylic acid esters Lactams Lactones Oxacyclic compounds Azacyclic compounds Monocarboxylic acids and derivatives Carbonyl compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Organonitrogen compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Cyclic depsipeptide - Phenylalanine or derivatives - Macrolide lactam - Alpha-amino acid ester - Macrolactam - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - Monocyclic benzene moiety - Fatty amide - Fatty acyl - N-acyl-amine - Benzenoid - Tertiary carboxylic acid amide - Pyrrolidine - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid ester - Lactam - Lactone - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Oxacycle - Azacycle - Organonitrogen compound - Carbonyl group - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic oxide - Organic oxygen compound - Organooxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. |
| External Descriptors | Not available |
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| Solubility | Soluble in ethanol, methanol, DMF, DMSO, and aqueous solutions (sparingly). |
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| Refractive Index | n20D1.61 (Predicted) |
| Boil Point(°C) | ~1086.9° C at 760 mmHg (Predicted) |
