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 antibacterial. It has activity against Gram-positive and -negative bacteria, including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae, and Diplococcus pneumoniae.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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/)

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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

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/)
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
Specialist databases
Antibiotic DB Antibiotic DB Database logo Oxytetracycline (terramycin)
Other databases
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
Search Google for chemical match using the InChIKey OWFJMIVZYSDULZ-PXOLEDIWSA-N
Search Google for chemicals with the same backbone OWFJMIVZYSDULZ
Search PubMed clinical trials oxytetracycline
Search PubMed titles oxytetracycline
Search PubMed titles/abstracts oxytetracycline
UniChem Compound Search for chemical match using the InChIKey OWFJMIVZYSDULZ-PXOLEDIWSA-N
UniChem Connectivity Search for chemical match using the InChIKey OWFJMIVZYSDULZ-PXOLEDIWSA-N