oxytetracycline   Click here for help

GtoPdb Ligand ID: 10919

Synonyms: E703 | NSC-9169 | Terramycin®
Approved drug PDB Ligand
oxytetracycline is an approved drug (FDA (1964), UK (2011))
Compound class: Synthetic organic
Comment: Oxytetracycline is a tetracycline class antibiotic. It has activity against Gram-positive and -negative bacteria, including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae, and Diplococcus pneumoniae.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 7
Rotatable bonds 2
Topological polar surface area 201.85
Molecular weight 460.15
XLogP -0.77
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]1[C@@H](O)[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]1[C@@H](O)[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O)O)C(=O)N)C
InChI InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25-26,28,30,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1
InChI Key OWFJMIVZYSDULZ-PXOLEDIWSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1964), UK (2011))
Withdrawn drug? Yes
IUPAC Name Click here for help
(4S,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
103 oxytetracycline
Synonyms Click here for help
E703 | NSC-9169 | Terramycin®
Database Links Click here for help
BindingDB Ligand 241973
CAS Registry No. 79-57-2 (source: PubChem)
ChEMBL Ligand CHEMBL1517
DrugBank Ligand DB00595
GtoPdb PubChem SID 405560360
PubChem CID 54675779
RCSB PDB Ligand OTC
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