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dihydrocodeine   Click here for help

GtoPdb Ligand ID: 7594

Synonyms: DF-118 | Dicogesic® | dihydrocodeine bitartrate | Drocode | Paracodeine®
Approved drug
dihydrocodeine is an approved drug (FDA (1958, as bitartrate with aspirin and caffeine))
Compound class: Synthetic organic
Comment: Dihydrocodeine is a semi-synthetic opioid analgesic.
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View more information in the IUPHAR Pharmacology Education Project: dihydrocodeine

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 2
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 41.93
Molecular weight 301.17
XLogP 1.06
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)C4CCC1O)C
Isomeric SMILES COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4CC[C@@H]1O)C
InChI InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
InChI Key RBOXVHNMENFORY-DNJOTXNNSA-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 (1958)
IUPAC Name Click here for help
(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol
International Nonproprietary Names Click here for help
INN number INN
728 dihydrocodeine
Synonyms Click here for help
DF-118 | Dicogesic® | dihydrocodeine bitartrate | Drocode | Paracodeine®
Database Links Click here for help
CAS Registry No. 125-28-0
ChEMBL Ligand CHEMBL1595
DrugBank Ligand DB01551
DrugCentral Ligand 886
GtoPdb PubChem SID 223365929
PubChem CID 5284543
Search Google for chemical match using the InChIKey RBOXVHNMENFORY-DNJOTXNNSA-N
Search Google for chemicals with the same backbone RBOXVHNMENFORY
Search PubMed clinical trials dihydrocodeine
Search PubMed titles dihydrocodeine
Search PubMed titles/abstracts dihydrocodeine
UniChem Compound Search for chemical match using the InChIKey RBOXVHNMENFORY-DNJOTXNNSA-N
UniChem Connectivity Search for chemical match using the InChIKey RBOXVHNMENFORY-DNJOTXNNSA-N
Wikipedia Dihydrocodeine