Compound ID | 1533

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Muraminomicin F

Class: Nucleoside analogue

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor. Inhibits transfer of the peptidoglycan precursor moiety (MurNAc-pentapeptide) to the membrane lipid carrier, undecaprenyl phosphate; MraY inhibitor
Target Pathogen: Active against Staphylococcus aureus
Description: Natural product from Streptosporangium sp.; muraminomicin derivative
Institute where first reported: Medicinal Chemistry Research Laboratories, Daiichi Sankyo Co., Ltd., Tokyo, Japan
Year first mentioned: 2019
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1186.3
Iso. SMILES: CCCCCCCCCCCC(CC(=O)OC1CN(C(C(=O)N(C1C(=O)O)C)C([C@@H]2[C@H](C[C@@H](O2)N3C=CC(=O)NC3=O)O)O[C@H]4C[C@@H]([C@H](O4)CN)O)C)OC(=O)CC(C)CC(=O)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)CC)OC)OC(=O)CCC(=O)O)OC
InChI Key: NFLAQRQUPWGKJN-CHFJNQTASA-N
Can. SMILES: CCCCCCCCCCCC(CC(=O)OC1CN(C)C(C([C@@H]2[C@H](C[C@H](N3C=CC(=O)NC3=O)O2)O)O[C@H]4C[C@@H]([C@@H](CN)O4)O)C(=O)N(C)C1C(=O)O)OC(=O)CC(C)CC(=O)O[C@H]5[C@@H]([C@@H]([C@H]([C@H](CC)O5)OC)OC(=O)CCC(=O)O)OC
InChI: InChI=1S/C55H87N5O23/c1-8-10-11-12-13-14-15-16-17-18-31(76-41(67)23-30(3)24-42(68)82-54-51(75-7)50(48(74-6)34(9-2)79-54)81-40(66)20-19-39(64)65)25-43(69)77-36-29-58(4)46(52(70)59(5)45(36)53(71)72)49(83-44-27-32(61)35(28-56)78-44)47-33(62)26-38(80-47)60-22-21-37(63)57-55(60)73/h21-22,30-36,38,44-51,54,61-62H,8-20,23-29,56H2,1-7H3,(H,64,65)(H,71,72)(H,57,63,73)/t30?,31?,32-,33-,34-,35+,36?,38+,44-,45?,46?,47-,48-,49?,50+,51+,54-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/145720731
Guide to Pharmacology: muraminomicin F
Citation: https://www.nature.com/articles/s41429-019-0235-3

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