doxycycline   

GtoPdb Ligand ID: 6464

Synonyms: BMY-28689 | Monodox® | Vibramycin®
doxycycline is an approved drug (FDA (1967), UK (2000))
Compound class: Synthetic organic
Comment: Doxycycline is a tetracycline based antibiotic. It has been repurposed as a low-potency human metalloprotease inhibitor for periodontitis and is also used as an antimalarial therapy.
There are a number of salt forms in PubChem. The chemical structure we show here matches that of the consensus structure in PubChem, listed in the links table below. The DrugBank, ChEBI, ChEMBL and PDB entries for doxycycline show a different structure.
Doxycycline is one of the key access group antibacterials on the World Health Organisation's List of Essential Medicines (link provided in the Classification table below).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure

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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Click here for structure editor
Physico-chemical Properties

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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 9
Hydrogen bond donors 6
Rotatable bonds 2
Topological polar surface area 181.62
Molecular weight 444.15
XLogP 0.39
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey

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.

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Canonical SMILES CN(C1C(=O)C(=C(C2(C1C(O)C1C(C)c3cccc(c3C(=C1C2=O)O)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]1[C@@H](C)c3cccc(c3C(=C1C2=O)O)O)O)O)C(=O)N)C
InChI InChI=1S/C22H24N2O8/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/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1
InChI Key SGKRLCUYIXIAHR-AKNGSSGZSA-N
Classification
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1967), UK (2000))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
International Nonproprietary Names
INN number INN
2125 doxycycline
Synonyms
BMY-28689 | Monodox® | Vibramycin®
Database Links
CAS Registry No. 564-25-0 (source: PubChem)
ChEBI CHEBI:50845
ChEMBL Ligand CHEMBL1433
DrugBank Ligand DB00254
GtoPdb PubChem SID 178103078
PubChem CID 54671203
RCSB PDB Ligand DXT
Search Google for chemical match using the InChIKey SGKRLCUYIXIAHR-AKNGSSGZSA-N
Search Google for chemicals with the same backbone SGKRLCUYIXIAHR
Search PubMed clinical trials doxycycline
Search PubMed titles doxycycline
Search PubMed titles/abstracts doxycycline
Search UniChem for chemical match using the InChIKey SGKRLCUYIXIAHR-AKNGSSGZSA-N
Search UniChem for chemicals with the same backbone SGKRLCUYIXIAHR
Wikipedia Doxycycline