zifanocycline   Click here for help

GtoPdb Ligand ID: 12794

Synonyms: KBP-7072
Compound class: Synthetic organic
Comment: Zifanocycline is an aminomethylcycline (tetracycline derivative) with broad-spectrum antibacterial activity [3]. We show the chemical structure provided by PubChem, but note that this is not an exact match for the CAS number assigned in the WHO INN record for this drug.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 11
Hydrogen bond donors 5
Rotatable bonds 5
Topological polar surface area 167.87
Molecular weight 552.62
XLogP 0.55
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CN(C)C1=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C(C(=C1)CN5CC6CC6C5)O)O)O)O)C(=O)N)N(C)C
Isomeric SMILES CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=C(C(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)CN5CC6CC6C5)N(C)C
InChI InChI=1S/C29H36N4O7/c1-31(2)18-8-15(11-33-9-13-5-14(13)10-33)23(34)20-16(18)6-12-7-17-22(32(3)4)25(36)21(28(30)39)27(38)29(17,40)26(37)19(12)24(20)35/h8,12-14,17,22,34-35,38,40H,5-7,9-11H2,1-4H3,(H2,30,39)/t12-,13?,14?,17-,22-,29-/m0/s1
InChI Key LBKXOQRVWDAQSX-OMBSCLNISA-N
Bioactivity Comments
Zifanocycline has potent in vitro activity against both Gram-positive and Gram-negative bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) isolates (MIC90 of 0.12 μg/ml) and Haemophilus influenzae (MIC90 of 0.25 μg/ml) [3]. The MIC90 for in vitro antibacterial activity against Acinetobacter baumannii clinical isolates is 1μg/ml [1-2].