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phenprocoumon   Click here for help

GtoPdb Ligand ID: 6839

Synonyms: Liquamar® | phenprocoumarol
Approved drug
phenprocoumon is an approved drug (FDA (1957))
Compound class: Synthetic organic
Comment: Vitamin K epoxide reductase complex subunit 1 isoform 1 inhibitor. The INN-designated compound is a racemic mixture of two enantiomers.The structure shown here does not specify stereochemistry and represents the mixture.
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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 1
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 50.44
Molecular weight 280.11
XLogP 4.99
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 CCC(c1c(=O)oc2c(c1O)cccc2)c1ccccc1
Isomeric SMILES CCC(c1c(=O)oc2c(c1O)cccc2)c1ccccc1
InChI InChI=1S/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,19H,2H2,1H3
InChI Key DQDAYGNAKTZFIW-UHFFFAOYSA-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 (1957)
Withdrawn drug? Yes
IUPAC Name Click here for help
4-hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
International Nonproprietary Names Click here for help
INN number INN
247 phenprocoumon
Synonyms Click here for help
Liquamar® | phenprocoumarol
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9035040
Reactome Reaction Reactome logo R-HSA-9026967
Other databases
CAS Registry No. 435-97-2
DrugBank Ligand DB00946
DrugCentral Ligand 2138
GtoPdb PubChem SID 178103445
PubChem CID 54680692
Search Google for chemical match using the InChIKey DQDAYGNAKTZFIW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone DQDAYGNAKTZFIW
Search PubMed clinical trials phenprocoumon
Search PubMed titles phenprocoumon
Search PubMed titles/abstracts phenprocoumon
UniChem Compound Search for chemical match using the InChIKey DQDAYGNAKTZFIW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey DQDAYGNAKTZFIW-UHFFFAOYSA-N
Wikipedia Phenprocoumon

Product suppliers

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MedChemExpress
Phenprocoumon (links to external site)
Cat. No. HY-A0145