metacycline

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Ligands
metacycline

GtoPdb Ligand ID: 13618

Synonyms: GS-2876 | methacycline | methylenecycline | Physiomycine® | Rondomycin®

metacycline is an approved drug (France)

Comment: Metacycline is a tetracycline antibacterial compound, derived from oxytetracycline [1]. Note that the structure shown here matches the CAS-assigned structure. The PubChem link, provided in the table below, is to their standardized chemical structure (CID 54675785), although this is not an exact structural match.

2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	10
Hydrogen bond donors	6
Rotatable bonds	2
Topological polar surface area	181.62
Molecular weight	442.42
XLogP	-0.56
No. Lipinski's rules broken	1

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	C=C1C2=CC=CC(=C2C(=O)C3=C([C@]4([C@]([H])([C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)[C@H]([C@]13[H])O)O)O)O
Isomeric SMILES	O[C@]12[C@]([C@H](N(C)C)C(O)=C(C(N)=O)C1=O)([C@@H](O)[C@]3(C(=C2O)C(=O)C=4C(C3=C)=CC=CC4O)[H])[H]
InChI	InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1
InChI Key	MHIGBKBJSQVXNH-IWVLMIASSA-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/)