omadacycline   Click here for help

GtoPdb Ligand ID: 10839

Synonyms: amadacycline | compound 6 [PMID: 21302930] | Nuzyra® | PTK-0796 | PTK0796
Approved drug PDB Ligand
omadacycline is an approved drug (FDA (2018))
Compound class: Synthetic organic
Comment: Omadacycline (PTK-0796) is an oral, tetracycline-like antibacterial [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 6
Rotatable bonds 7
Topological polar surface area 176.66
Molecular weight 556.29
XLogP 2.54
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1C[C@@H]1Cc3c(cc(c(c3C(=C1C2=O)O)O)CNCC(C)(C)C)N(C)C)O)O)C(=O)N)C
Isomeric SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1C[C@@H]1Cc3c(cc(c(c3C(=C1C2=O)O)O)CNCC(C)(C)C)N(C)C)O)O)C(=O)N)C
InChI InChI=1S/C29H40N4O7/c1-28(2,3)12-31-11-14-10-17(32(4)5)15-8-13-9-16-21(33(6)7)24(36)20(27(30)39)26(38)29(16,40)25(37)18(13)23(35)19(15)22(14)34/h10,13,16,21,31,34-35,38,40H,8-9,11-12H2,1-7H3,(H2,30,39)/t13-,16-,21-,29-/m0/s1
InChI Key VJYKVCURWJGLPG-IQZGDKDPSA-N
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Summary of Clinical Use Click here for help
Omadacycline is used to treat pneumonia or skin infections caused by susceptible bacteria. The application to the EMA for marketing authorisation for omadacycline (for the treatment of skin and skin structure infections) was withdrawn in October 2019 [2].
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