tigecycline

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Ligands
tigecycline

GtoPdb Ligand ID: 10929

Synonyms: GAR-936 | GAR936 | TBG-MINO | Tygacil® | WAY-GAR-936

tigecycline is an approved drug (FDA (2005), EMA & UK (2006))

Compound class: Synthetic organic

Comment: Tigecycline is a first-in-class glycylcycline (tetracycline) antibacterial derived from minocycline [5,7]. It was designed to overcome efflux and ribosomal protection mechanisms of resistance that have emerged against the tetracycline class of compounds.

tigecycline is commercially available from our sponsors

2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	12
Hydrogen bond donors	7
Rotatable bonds	8
Topological polar surface area	205.76
Molecular weight	585.28
XLogP	1.39
No. Lipinski's rules broken	2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey

Canonical SMILES	O=C(Nc1cc(N(C)C)c2c(c1O)C(=C1[C@@H](C2)C[C@@H]2[C@@](C1=O)(O)C(=C(C(=O)[C@H]2N(C)C)C(=O)N)O)O)CNC(C)(C)C
Isomeric SMILES	O=C(Nc1cc(N(C)C)c2c(c1O)C(=C1[C@@H](C2)C[C@@H]2[C@@](C1=O)(O)C(=C(C(=O)[C@H]2N(C)C)C(=O)N)O)O)CNC(C)(C)C
InChI	InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36-37,40,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1
InChI Key	SOVUOXKZCCAWOJ-HJYUBDRYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)