Compound ID | 418

Update compound information

CB-182,548

Synonym(s): CB-182548

Class: Lipopeptide

Spectrum of activity: Gram-negative
Details of activity: Cell wall modulators; derived from daptomycin. Cubist were searching for a compound that had similar activity as daptomcyin and it's analogue A54145E against S pneumoniae but without the issues of being inhibited by surfactant and toxicity respectively, a series of compounds were generated. CB-182548 had similar activities as daptomcyin and had improved activity in the presence of surfactant .
Institute where first reported: Cubist Pharmaceuticals (Merck & Co, USA)
Highest developmental phase: Preclinical
Development status: Inactive
Reason Dropped: Was not as potent as vancomycin in trials
Chemical structure(s):
Click here for structure editor
Molecular weight: 1615.74
Iso. SMILES: CCCCCCCCCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C(=O)N)O)C(=O)N[C@H]3[C@@H](OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CN(C3=O)C)C)CC(=O)O)CCCCN)[C@@H](C(=O)O)OC)C)[C@H](C)CC(=O)O)[C@@H](C)CC)C
InChI Key: BXDMYCCYPDAQGW-KOXZZYNASA-N
Can. SMILES: CCCCCCCCCC(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C(=O)N)O)C(=O)N[C@H]3[C@H](C)OC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H]([C@H](C)CC(=O)O)NC(=O)[C@@H](C)NC(=O)CNC(=O)[C@H]([C@@H](C(=O)O)OC)NC(=O)[C@@H](CCCCN)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C)NC(=O)CN(C)C3=O
InChI: InChI=1S/C72H110N16O26/c1-10-12-13-14-15-16-17-25-47(89)79-45(30-40-32-75-42-23-19-18-22-41(40)42)65(104)81-44(26-27-50(92)93)64(103)86-56(58(98)60(74)99)69(108)85-55-39(7)114-72(112)54(35(3)11-2)84-68(107)53(36(4)29-51(94)95)83-62(101)38(6)77-48(90)33-76-67(106)57(59(113-9)71(110)111)87-63(102)43(24-20-21-28-73)80-66(105)46(31-52(96)97)82-61(100)37(5)78-49(91)34-88(8)70(55)109/h18-19,22-23,32,35-39,43-46,53-59,75,98H,10-17,20-21,24-31,33-34,73H2,1-9H3,(H2,74,99)(H,76,106)(H,77,90)(H,78,91)(H,79,89)(H,80,105)(H,81,104)(H,82,100)(H,83,101)(H,84,107)(H,85,108)(H,86,103)(H,87,102)(H,92,93)(H,94,95)(H,96,97)(H,110,111)/t35-,36+,37-,38+,39-,43+,44+,45-,46-,53-,54-,55-,56-,57-,58-,59-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/52943529
Citations:
  • https://books.google.co.uk/books?id=FTwnAQAAQBAJ&pg=PA128&lpg=PA128&dq=CB+182561&source=bl&ots=pI-Xz9YypC&sig=mAMPQDkmd51VwwUmAKhWLM8Oq9w&hl=en&sa=X&ei=bmONVbm_FMz9ULqsgogC&ved=0CCEQ6AEwAA#v=onepage&q=CB%20182561&f=false
  • https://journals.asm.org/doi/10.1128/aac.01307-09?url_ver=Z39.88-2003&rfr_id=ori%3Arid%3Acrossref.org&rfr_dat=cr_pub++0pubmed

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