pholcodine   Click here for help

GtoPdb Ligand ID: 9086

Synonyms: Covonia Dry Cough® | Galenphol® | Pavacol-D®
Approved drug
pholcodine is an approved drug (UK (1993))
Compound class: Synthetic organic
Comment: Pholcodine is an opioid cough suppressant (antitussive). It helps suppress unproductive coughs, has a mild sedative effect, but very limited analgesic effects.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: pholcodine

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 54.4
Molecular weight 398.22
XLogP 0.26
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
Click here for help

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/)

✖
Canonical SMILES CN1CCC23C4C1Cc1c3c(OC2C(C=C4)O)c(cc1)OCCN1CCOCC1
Isomeric SMILES CN1CC[C@@]23[C@@H]4[C@H]1Cc1c3c(O[C@H]2[C@H](C=C4)O)c(cc1)OCCN1CCOCC1
InChI InChI=1S/C23H30N2O4/c1-24-7-6-23-16-3-4-18(26)22(23)29-21-19(5-2-15(20(21)23)14-17(16)24)28-13-10-25-8-11-27-12-9-25/h2-5,16-18,22,26H,6-14H2,1H3/t16-,17+,18-,22-,23-/m0/s1
InChI Key GPFAJKDEDBRFOS-FKQDBXSBSA-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. UK (1993)
IUPAC Name Click here for help
(4R,4aR,7S,7aR,12bS)-3-methyl-9-(2-morpholin-4-ylethoxy)-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-o
International Nonproprietary Names Click here for help
INN number INN
272 pholcodine
Synonyms Click here for help
Covonia Dry Cough® | Galenphol® | Pavacol-D®
Database Links Click here for help
CAS Registry No. 509-67-1 (source: PubChem)
ChEMBL Ligand CHEMBL2105224
DrugBank Ligand DB09209
DrugCentral Ligand 2154
GtoPdb PubChem SID 315661171
PubChem CID 5311356
Search Google for chemical match using the InChIKey GPFAJKDEDBRFOS-FKQDBXSBSA-N
Search Google for chemicals with the same backbone GPFAJKDEDBRFOS
Search PubMed clinical trials pholcodine
Search PubMed titles pholcodine
Search PubMed titles/abstracts pholcodine
UniChem Compound Search for chemical match using the InChIKey GPFAJKDEDBRFOS-FKQDBXSBSA-N
UniChem Connectivity Search for chemical match using the InChIKey GPFAJKDEDBRFOS-FKQDBXSBSA-N
Wikipedia Pholcodine