Compound ID | 2760

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Telomycin

Synonym(s): Telomicin

Class: Antimicrobial peptide

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Membrane-active agent. Targets phospholipid cardiolipin in bacterial membrane
Target Pathogen: Active against Streptococcus agalactiae, Diplococcus penumoniae, Bacillus anthracis, Staphylococcus aureus, and Corynebacterium xerosis
Description: Natural product from Streptomyces sp. (also by Micromonospora schwarzwaldensis and Streptomyces coeruleorubidus); selectively toxic as demonstrated in tissue culture
Institute where first reported: Bristol-Myers
Year first mentioned: 1957
Development status: Experimental
Chemical structure(s):
Click here for structure editor
Molecular weight: 1286.35
Iso. SMILES: CC1C(C(=O)NC(C(=O)NC(C(=O)NCC(=O)N2CCC(C2C(=O)NC(=CC3=CNC4=CC=CC=C43)C(=O)NC(C(=O)NC(C(=O)N5CCC(C5C(=O)O1)O)C(C(C)C)O)C(C)C6=CNC7=CC=CC=C76)O)C)C(C)O)CNC(=O)C(CO)NC(=O)CC(C(=O)O)N
InChI Key: NAUSZDMZRHELKZ-UHFFFAOYSA-N
Can. SMILES: CC(C)C(C1C(=O)N2CCC(C2C(=O)OC(C)C(CNC(=O)C(CO)NC(=O)CC(C(=O)O)N)C(=O)NC(C(C)O)C(=O)NC(C)C(=O)NCC(=O)N3CCC(C3C(=O)NC(=CC4=CNC5=C4C=CC=C5)C(=O)NC(C(C)C6=CNC7=C6C=CC=C7)C(=O)N1)O)O)O
InChI: InChI=1S/C60H79N13O19/c1-26(2)50(80)47-58(88)73-18-16-42(77)49(73)60(91)92-30(6)35(23-64-53(83)40(25-74)67-43(78)20-36(61)59(89)90)52(82)70-46(29(5)75)56(86)66-28(4)51(81)65-24-44(79)72-17-15-41(76)48(72)57(87)68-39(19-31-21-62-37-13-9-7-11-32(31)37)54(84)69-45(55(85)71-47)27(3)34-22-63-38-14-10-8-12-33(34)38/h7-14,19,21-22,26-30,35-36,40-42,45-50,62-63,74-77,80H,15-18,20,23-25,61H2,1-6H3,(H,64,83)(H,65,81)(H,66,86)(H,67,78)(H,68,87)(H,69,84)(H,70,82)(H,71,85)(H,89,90)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/99830
Citations:
  • https://patentimages.storage.googleapis.com/35/f2/72/51201dd8250318/US3061516.pdf
  • https://pubs.acs.org/doi/10.1021/jacs.5b01794
  • https://pubs.rsc.org/en/content/articlelanding/2024/qo/d3qo01411h#:~:text=Telomycin%2C%20a%20nonribosomal%20cyclic%20depsipeptide,the%20bacterial%20dimeric%20phospholipid%20cardiolipin.

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