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oxycodone   Click here for help

GtoPdb Ligand ID: 7093

Synonyms: oxycodone hydrochloride | Roxicodone®
Approved drug PDB Ligand
oxycodone is an approved drug (FDA (1998))
Compound class: Synthetic organic
Comment: Oxycodone is an opioid drug. It is a semi-synthetic derivative of thebaine.
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View more information in the IUPHAR Pharmacology Education Project: oxycodone

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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Click here for structure editor
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 3
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 59
Molecular weight 315.15
XLogP 0.01
No. Lipinski's rules broken 0

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 COc1ccc2c3c1OC1C43CCN(C(C2)C4(O)CCC1=O)C
Isomeric SMILES COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@]4(O)CCC1=O)C
InChI InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1
InChI Key BRUQQQPBMZOVGD-XFKAJCMBSA-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. US FDA (1998)
IUPAC Name Click here for help
(4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
International Nonproprietary Names Click here for help
INN number INN
1701 oxycodone
Synonyms Click here for help
oxycodone hydrochloride | Roxicodone®
Database Links Click here for help
CAS Registry No. 76-42-6
ChEBI CHEBI:7852
ChEMBL Ligand CHEMBL656
DrugBank Ligand DB00497
DrugCentral Ligand 2029
GtoPdb PubChem SID 178103671
PubChem CID 5284603
RCSB PDB Ligand OOX
Search Google for chemical match using the InChIKey BRUQQQPBMZOVGD-XFKAJCMBSA-N
Search Google for chemicals with the same backbone BRUQQQPBMZOVGD
Search PubMed clinical trials oxycodone
Search PubMed titles oxycodone
Search PubMed titles/abstracts oxycodone
UniChem Compound Search for chemical match using the InChIKey BRUQQQPBMZOVGD-XFKAJCMBSA-N
UniChem Connectivity Search for chemical match using the InChIKey BRUQQQPBMZOVGD-XFKAJCMBSA-N
Wikipedia Oxycodone