Compound ID | 2991

Update compound information

MC-1

Class: Beta-lactam

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against carbapenem-resistant Pseudomonas aeruginosa
Propensity to select resistant mutants: Yes, at 9.3 x 10^-7 mutation frequency at 4xMIC
Description: Synthetic compound; antibacterial activity is not affected by 𝛽-lactamases, efflux pumps, or outer membrane permeability changes; siderophore-conjugated monocarbam
Institute where first reported: Antibacterials Research Unit, Pfizer Worldwide Research & Development, Groton, Connecticut, USA
Year first mentioned: 2010
Development status: Experimental
Chemical structure(s):
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Molecular weight: 714.64
Iso. SMILES: NC1=NC(/C(/C(N[C@@H]2C(N(C(NS(=O)(N3C(N(C[C@H](CO)O)C(C=4NC=C(O)C(C4)=O)=N3)=O)=O)=O)C2)=O)=O)=N/OC(C)(C)C(O)=O)=CS1
InChI Key: AALLRVSISIPCOY-CMHWWOLMSA-N
Can. SMILES: CC(C)(C(=O)O)O/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2CN(C2=O)C(=O)NS(=O)(=O)N3C(=O)N(C[C@H](CO)O)C(=N3)C4=CC(=O)C(=CN4)O
InChI: InChI=1S/C23H26N10O13S2/c1-23(2,19(40)41)46-29-15(12-8-47-20(24)27-12)17(38)26-11-6-32(18(11)39)21(42)30-48(44,45)33-22(43)31(5-9(35)7-34)16(28-33)10-3-13(36)14(37)4-25-10/h3-4,8-9,11,34-35,37H,5-7H2,1-2H3,(H2,24,27)(H,25,36)(H,26,38)(H,30,42)(H,40,41)/b29-15-/t9-,11+/m1/s1
External links:
Citations:
  • https://pubs.acs.org/doi/10.1021/ml200012f
  • https://journals.asm.org/doi/10.1128/aac.01345-12
  • https://www.pnas.org/doi/full/10.1073/pnas.1013092107

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