tetracycline   Click here for help

GtoPdb Ligand ID: 10927

Synonyms: achromycin | Ala-Tet® | Brodspec® | NSC-108579 | Panmycin® | Sumycin® | TCN
Approved drug
tetracycline is an approved drug (FDA (1953), UK (2001))
Compound class: Synthetic organic
Comment: Tetracycline is a long-used oral antibiotic. It has broad spectrum activity against aerobic and anaerobic bacteria, both Gram-negative and Gram-positive. Pseudomonas aeruginosa and Proteus spp. have natural resistance to tetracyclines. Acquired resistance to tetracycline is now commonplace.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 2
Topological polar surface area 181.62
Molecular weight 444.15
XLogP 0.26
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]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O)O)C(=O)N)C
Isomeric SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1C[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O)O)C(=O)N)C
InChI InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
InChI Key NWXMGUDVXFXRIG-WESIUVDSSA-N
References
1. Hamasuna R, Jensen JS, Osada Y. (2009)
Antimicrobial susceptibilities of Mycoplasma genitalium strains examined by broth dilution and quantitative PCR.
Antimicrob Agents Chemother, 53 (11): 4938-9. [PMID:19738019]