Compound ID | 972

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CB-182575

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 analog A54145E against S pneumoniae but without the issues of being inhibited by surfactant and toxicity respectively, a series of compounds were generated. CB-182575 was inhibited by surfactant only 2 fold .
Institute where first reported: Cubist Pharmaceuticals (Merck & Co, USA)
Year first mentioned: 2008
Highest development stage: Preclinical
Development status: Inactive
Reason dropped: Was not as potent as vancomycin in trials
Chemical structure(s):
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Molecular weight: 1657.78
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)CCCCN)CC(=O)O)C)C)NC(=O)[C@H]([C@@H](C(=O)N)O)NC(=O)[C@@H](CC(=O)N)NC(=O)[C@H](CC2=CNC3=CC=CC=C32)NC(=O)CCCCCCCC(C)C)C
InChI Key: UFGLBIDEQOFIBF-LEPDZAINSA-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](CCCCN)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](CC(=O)N)NC(=O)[C@H](CC2=CNC3=C2C=CC=C3)NC(=O)CCCCCCCC(C)C
InChI: InChI=1S/C73H112N18O26/c1-10-35(4)55-73(115)117-38(7)56(88-70(111)57(59(101)61(77)102)89-67(108)45(29-48(76)93)85-64(105)43(27-39-31-78-41-22-17-16-21-40(39)41)81-49(94)24-15-13-11-12-14-20-34(2)3)71(112)91(8)33-51(96)80-37(6)62(103)84-46(30-53(99)100)65(106)83-42(23-18-19-25-74)63(104)90-58(60(116-9)72(113)114)68(109)79-32-50(95)82-44(28-47(75)92)66(107)86-54(69(110)87-55)36(5)26-52(97)98/h16-17,21-22,31,34-38,42-46,54-60,78,101H,10-15,18-20,23-30,32-33,74H2,1-9H3,(H2,75,92)(H2,76,93)(H2,77,102)(H,79,109)(H,80,96)(H,81,94)(H,82,95)(H,83,106)(H,84,103)(H,85,105)(H,86,107)(H,87,110)(H,88,111)(H,89,108)(H,90,104)(H,97,98)(H,99,100)(H,113,114)/t35-,36+,37-,38-,42+,43-,44+,45+,46-,54-,55-,56-,57-,58-,59-,60-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/52949640
Citation: 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

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