Compound ID | 419

Update compound information

CB-182,549

Synonym(s): CB-182549

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-182549 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: 1631.69
Iso. SMILES: CC[C@H](C)[C@H]1C(=O)O[C@H]([C@@H](C(=O)N(CC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)NCC(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)[C@H](C)CC(=O)O)CC(=O)N)[C@@H](C(=O)O)OC)CO)CC(=O)O)C)C)NC(=O)[C@H]([C@@H](C(=O)N)O)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC2=CNC3=CC=CC=C32)NC(=O)CCCCCCCC(C)C)C
InChI Key: CURABDCELLBMAN-XUMYQJGHSA-N
Can. SMILES: CC[C@H](C)[C@H]1C(=O)O[C@@H](C)[C@@H](C(=O)N(C)CC(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](CO)C(=O)N[C@H]([C@@H](C(=O)O)OC)C(=O)NCC(=O)N[C@H](CC(=O)N)C(=O)N[C@@H]([C@H](C)CC(=O)O)C(=O)N1)NC(=O)[C@H]([C@@H](C(=O)N)O)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC2=CNC3=C2C=CC=C3)NC(=O)CCCCCCCC(C)C
InChI: InChI=1S/C71H106N16O28/c1-10-33(4)53-71(113)115-36(7)54(84-68(109)55(57(99)59(73)100)85-61(102)40(22-23-49(93)94)79-62(103)41(25-37-28-74-39-20-17-16-19-38(37)39)77-46(90)21-15-13-11-12-14-18-32(2)3)69(110)87(8)30-48(92)76-35(6)60(101)80-43(27-51(97)98)63(104)81-44(31-88)65(106)86-56(58(114-9)70(111)112)66(107)75-29-47(91)78-42(26-45(72)89)64(105)82-52(67(108)83-53)34(5)24-50(95)96/h16-17,19-20,28,32-36,40-44,52-58,74,88,99H,10-15,18,21-27,29-31H2,1-9H3,(H2,72,89)(H2,73,100)(H,75,107)(H,76,92)(H,77,90)(H,78,91)(H,79,103)(H,80,101)(H,81,104)(H,82,105)(H,83,108)(H,84,109)(H,85,102)(H,86,106)(H,93,94)(H,95,96)(H,97,98)(H,111,112)/t33-,34+,35-,36-,40+,41-,42+,43-,44+,52-,53-,54-,55-,56+,57-,58-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/52949639
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

    • AntibioticDB is supported by GARDP.

    If you have feedback, experience problems, or are interested in a collaboration, please contact us. | Terms and conditions

    The content of this site is intended for educational and scientific research purposes only and not as a source of medical advice or consultation.