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MYP_088863
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Basic Information
Daptomycin
Antimicrobial
Antimicrobial ▸ Antibacterial
Antimicrobial ▸ Antibacterial ▸ Anti-Gram-positive
Standard
13 amino acids
C61H84N16O26
Standard
Sequence
WNDTGKDADGSEY
Physicochemical Analysis
1457.41 Da
4.05
-3.24
-3.45
-0.2489
-1.85
0.35
-0.25
2.38
7.69
0.1538
6990.00
6990.00
The radar chart summarizes major physicochemical dimensions for quick comparison, while exact numerical values remain listed on the left.
Residue Composition
Amino Acid Composition
Chemical Descriptors
707.31
-9.16
24.0
23.0
46.0
103.0
3.0
13.0
Structural Visualization
3D PDB MODEL
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2D CHEMICAL STRUCTURE
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Experimental Records
RECORD: Rec_0035915 VERIFIED: YES
Provenance & Taxonomy
not reported [other]
Structure & Mods
linear peptide [Linear]
canonical L-amino-acid peptide [L]
Bio-Activity Profile
-
Escherichia coli TOP10
Mex pooled growth assay (OD_ID at 4.5 h; Wald adjusted p-value)
PaperKoch P, Schmitt S, Cardner M, Beerenwinkel N, Panke S, Held M. Discovery of antimicrobials by massively parallelized growth assays (Mex). Scientific Reports. 2022;12:4097. doi:10.1038/s41598-022-07755-7 PMID35260685 Evidence URLhttps://pubmed.ncbi.nlm.nih.gov/35260685/
RECORD: Rec_0065378 VERIFIED: YES
Provenance & Taxonomy
Streptomyces roseosporus [Bacterium]
Structure & Mods
head-to-tail cyclic peptide [Cyclic]
mixed L/D amino-acid peptide [Mixed]
Lipidation
Esterification
Daptomycin was approved by FDA in 2003 to treat soft-tissue infections, and in 2006 to treat S. aureus bacteremia and right-sided endocarditis. Warning: the sequence is a close mimic of the natural counterpart. Chemical modification: The natural form is cyclic due to the ester bond between the hydroxyl of T4 and the carboxyl of kynurenine-13 (represented by Y here). In daptomycin, the N-terminus is lipidated with n-decanoyl fatty acid chain to replace the C11 branched fatty acid in the natural form of A21978C1 (Eliopoulos GM et al., 1985). Other nonstandard amino acids include ornithine-6 (represented with K), (2S,3R)-3-methyl-glutamic acid-12 (represented with E), and three D-amino acids at positions N2, A8, and S11
Bio-Activity Profile
Antimicrobial
Listeria monocytogenes
4-16 μg/mL
MIC
PaperIn vitro and in vivo activity of LY 146032, a new cyclic lipopeptide antibiotic.
RECORD: Rec_0087064 VERIFIED: YES
Provenance & Taxonomy
Streptomyces roseosporus [Bacterium]
Structure & Mods
head-to-tail cyclic peptide [Cyclic]
mixed L/D amino-acid peptide [Mixed]
Lipidation
Esterification
Daptomycin was approved by FDA in 2003 to treat soft-tissue infections, and in 2006 to treat S. aureus bacteremia and right-sided endocarditis. Warning: the sequence is a close mimic of the natural counterpart. Chemical modification: The natural form is cyclic due to the ester bond between the hydroxyl of T4 and the carboxyl of kynurenine-13 (represented by Y here). In daptomycin, the N-terminus is lipidated with n-decanoyl fatty acid chain to replace the C11 branched fatty acid in the natural form of A21978C1 (Eliopoulos GM et al., 1985). Other nonstandard amino acids include ornithine-6 (represented with K), (2S,3R)-3-methyl-glutamic acid-12 (represented with E), and three D-amino acids at positions N2, A8, and S11
Bio-Activity Profile
Antimicrobial
Staphylococcus aureus, S. faecalis, Staphylococcus epidermidis
0.125-0.5 μg/mL
MIC
PaperIn vitro and in vivo activity of LY 146032, a new cyclic lipopeptide antibiotic.
RECORD: Rec_0152154 VERIFIED: YES
Provenance & Taxonomy
Streptomyces roseosporus [Bacterium]
Structure & Mods
head-to-tail cyclic peptide [Cyclic]
mixed L/D amino-acid peptide [Mixed]
Lipidation
Esterification
Daptomycin was approved by FDA in 2003 to treat soft-tissue infections, and in 2006 to treat S. aureus bacteremia and right-sided endocarditis. Warning: the sequence is a close mimic of the natural counterpart. Chemical modification: The natural form is cyclic due to the ester bond between the hydroxyl of T4 and the carboxyl of kynurenine-13 (represented by Y here). In daptomycin, the N-terminus is lipidated with n-decanoyl fatty acid chain to replace the C11 branched fatty acid in the natural form of A21978C1 (Eliopoulos GM et al., 1985). Other nonstandard amino acids include ornithine-6 (represented with K), (2S,3R)-3-methyl-glutamic acid-12 (represented with E), and three D-amino acids at positions N2, A8, and S11
Bio-Activity Profile
Antimicrobial
V. streptococci
<0.06-4 μg/mL
MIC
PaperIn vitro and in vivo activity of LY 146032, a new cyclic lipopeptide antibiotic.
RECORD: Rec_0341678 VERIFIED: YES
Provenance & Taxonomy
Streptomyces roseosporus [Bacterium]
Structure & Mods
head-to-tail cyclic peptide [Cyclic]
mixed L/D amino-acid peptide [Mixed]
Lipidation
Esterification
Daptomycin was approved by FDA in 2003 to treat soft-tissue infections, and in 2006 to treat S. aureus bacteremia and right-sided endocarditis. Warning: the sequence is a close mimic of the natural counterpart. Chemical modification: The natural form is cyclic due to the ester bond between the hydroxyl of T4 and the carboxyl of kynurenine-13 (represented by Y here). In daptomycin, the N-terminus is lipidated with n-decanoyl fatty acid chain to replace the C11 branched fatty acid in the natural form of A21978C1 (Eliopoulos GM et al., 1985). Other nonstandard amino acids include ornithine-6 (represented with K), (2S,3R)-3-methyl-glutamic acid-12 (represented with E), and three D-amino acids at positions N2, A8, and S11
Bio-Activity Profile
Antimicrobial
S. pyogenes
<0.06 μg/mL
MIC
PaperIn vitro and in vivo activity of LY 146032, a new cyclic lipopeptide antibiotic.
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