Compound ID | 3624

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Aminoacyl adenylate mimic

Class: Protein synthesis inhibitor

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive, Gram-negative & Antimycobacterial
Mechanism of action: Protein synthesis inhibitor. Aminoacyl-tRNA synthetase inhibitor (isoleucyl-tRNA synthetase [Ile-RS] inhibitor)
Target Pathogen: Active against Staphylococcus aureus, Enterococcus sp., Streptococcus sp., Haemophilus influenzae, Escherichia coli, Mycoplasma sp., and Mycobacterium tuberculosis
Description: Synthetic compound; analogues reported; also binds to fungal and parasitic aminoacyl-tRNA synthetases
Institute where first reported: Cubist Pharmaceuticals, Inc. US
Year first mentioned: 1997
Development status: Experimental
Chemical structure(s):
Click here for structure editor
Molecular weight: 604.68
Iso. SMILES: CC[C@H](C)[C@@H](C(=O)NS(=O)(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)CCN2N=C(N=N2)CC3=CC=C(C=C3)OC4=CC=CC=C4)O)O)N
InChI Key: ZTUNESQXNPOBAT-ULWHLVFWSA-N
Can. SMILES: CC[C@H](C)[C@@H](C(=O)NS(=O)(=O)OC[C@@H]1[C@H]([C@H]([C@H](CCN2N=C(CC3=CC=C(C=C3)OC4=CC=CC=C4)N=N2)O1)O)O)N
InChI: InChI=1S/C27H36N6O8S/c1-3-17(2)24(28)27(36)31-42(37,38)39-16-22-26(35)25(34)21(41-22)13-14-33-30-23(29-32-33)15-18-9-11-20(12-10-18)40-19-7-5-4-6-8-19/h4-12,17,21-22,24-26,34-35H,3,13-16,28H2,1-2H3,(H,31,36)/t17-,21-,22+,24-,25-,26+/m0/s1
External links:
Structure link: https://pubchem.ncbi.nlm.nih.gov/compound/483208
Citation: https://patents.google.com/patent/WO1997005132A1/en?oq=WO%2f1997%2f005132
Patent: WO1997005132A1

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