Compound ID | 420

Update compound information

CB-182,561

Synonym(s): CB-182561

Class: Lipopeptide

Agent Type: Natural product;
Spectrum of activity: Gram-positive
Mechanism of action: Membrane-active agent. Cell wall modulator
Target Pathogen: Active against Streptococcus pneumoniae
Description: Natural product from Streptomyces fradiae whose A54145 lipopeptide biosynthetic gene cluster is engineered to produce recombinant/hybrid lipopeptide; Cubist was searching for a compound that had similar activity as daptomcyin and it's analogue A54145E against Streptococcus pneumoniae but without the issues of being inhibited by surfactant and toxicity respectively
Institute where first reported: Cubist Pharmaceuticals (Merck & Co, USA)
Year first mentioned: 2008
Development status: Experimental
Reason dropped: Was not as potent as vancomycin in mouse model of pneumonia
Chemical structure(s):
Click here for structure editor
Molecular weight: 1612.74
Iso. SMILES: C[C@H]1[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)N[C@H](C(=O)O1)C(C)C)[C@H](C)CC(=O)O)CC(=O)N)CC(=O)OC)CCCCN)CC(=O)O)C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H](CC(=O)N)NC(=O)[C@H](CC2=CNC3=CC=CC=C32)NC(=O)CCCCCCCC(C)C
InChI Key: RNRQYDJGCOFNCC-AKGYBTMVSA-N
Can. SMILES: CC(C)CCCCCCCC(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N[C@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H]3[C@H](C)OC(=O)[C@H](C(C)C)NC(=O)[C@H]([C@H](C)CC(=O)O)NC(=O)[C@@H](CC(=O)N)NC(=O)CNC(=O)[C@H](CC(=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/C72H109N17O25/c1-35(2)19-13-11-10-12-14-23-52(92)79-44(26-40-32-76-42-21-16-15-20-41(40)42)65(105)83-46(28-51(75)91)66(106)84-48(30-57(99)100)69(109)88-61-39(7)114-72(112)59(36(3)4)86-70(110)60(37(5)25-55(95)96)87-68(108)45(27-50(74)90)80-53(93)33-77-63(103)49(31-58(101)113-9)85-64(104)43(22-17-18-24-73)81-67(107)47(29-56(97)98)82-62(102)38(6)78-54(94)34-89(8)71(61)111/h15-16,20-21,32,35-39,43-49,59-61,76H,10-14,17-19,22-31,33-34,73H2,1-9H3,(H2,74,90)(H2,75,91)(H,77,103)(H,78,94)(H,79,92)(H,80,93)(H,81,107)(H,82,102)(H,83,105)(H,84,106)(H,85,104)(H,86,110)(H,87,108)(H,88,109)(H,95,96)(H,97,98)(H,99,100)/t37-,38+,39+,43-,44+,45-,46-,47+,48+,49+,59+,60+,61+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/52942327
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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