Compound ID | 761

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MDL 62,879

Synonym(s): GE2270A  |  MDL 62879  |  GE2270 A

Class: Antimicrobial peptide

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive & Antimycobacterial
Mechanism of action: Protein synthesis inhibitor. Elongation Factor Tu inhibitor; EF-Tu inhibitor
Target Pathogen: Active against Staphylococcus aureus, Enterococci, and Mycobacterium tuberculosis
Description: Natural product from Planobispora rosea; Soffientini A, Landini P, Denaro M and Islam K. Bacterial protein synthesis inhibitor MDL 62879 induces a conformational change in elongation factor Tu (Ef-Tu) and inhibits binding pf aa-tRNA. 33rd-Intersci-Conf-Antimicrobial-Agents-Chemother 1993; 201.
Institute where first reported: Aventis (Sanofi Aventis, France)
Year first mentioned: 1993
Highest development stage: Preclinical
Development status: Experimental
Reason dropped: Shows poor aqueous solubility
Chemical structure(s):
Click here for structure editor
Molecular weight: 1276.5
Iso. SMILES: CC1=C2C(=O)NC(C3=NC(=C(S3)COC)C(=O)NCC(=O)NC(C4=NC(=CS4)C5=NC(=CS5)C6=C(C=CC(=N6)C7=NC(=CS7)C8=NC(CO8)C(=O)N9CCCC9C(=O)N)C%10=NC(=CS%10)C(=O)NC(C(=N2)S1)CC(=O)N)C(C%11=CC=CC=C%11)O)C(C)C
InChI Key: JMKLDKKRJNPACS-UHFFFAOYSA-N
Can. SMILES: CC(C)C1C2=NC(=C(COC)S2)C(=O)NCC(=O)NC(C(C3=CC=CC=C3)O)C4=NC(=CS4)C5=NC(=CS5)C6=NC(=CC=C6C7=NC(=CS7)C(=O)NC(CC(=O)N)C8=NC(=C(C)S8)C(=O)N1)C9=NC(=CS9)C%10=NC(CO%10)C(=O)N%11CCCC%11C(=O)N
InChI: InChI=1S/C55H53N15O10S6/c1-23(2)38-54-69-41(35(86-54)18-79-4)46(76)58-16-37(72)66-42(43(73)25-9-6-5-7-10-25)53-65-33(22-84-53)51-62-30(19-82-51)40-26(49-63-31(20-81-49)45(75)60-28(15-36(56)71)52-68-39(24(3)85-52)47(77)67-38)12-13-27(59-40)50-64-32(21-83-50)48-61-29(17-80-48)55(78)70-14-8-11-34(70)44(57)74/h5-7,9-10,12-13,19-23,28-29,34,38,42-43,73H,8,11,14-18H2,1-4H3,(H2,56,71)(H2,57,74)(H,58,76)(H,60,75)(H,66,72)(H,67,77)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/16147064
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/9016775/
  • https://pubs.acs.org/doi/10.1021/bi0525122
  • https://doi.org/10.1002/j.1460-2075.1991.tb08009.x

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