udenafil   Click here for help

GtoPdb Ligand ID: 11577

Synonyms: DA-8159 | DA8159 | Zydena®
Approved drug
udenafil is an approved drug (South Korea)
Compound class: Synthetic organic
Comment: Udenafil (DA-8159) is an oral PDE5 inhibitor that was developed by Dong-A Pharmaceutical Company for erectogenic potential [1,3-4].
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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

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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 6
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 130.59
Molecular weight 516.25
XLogP 3.13
No. Lipinski's rules broken 1

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 CCCOc1ccc(cc1c1nc2c(CCC)nn(c2c(=O)[nH]1)C)S(=O)(=O)NCCC1CCCN1C
Isomeric SMILES CCCOc1ccc(cc1c1nc2c(CCC)nn(c2c(=O)[nH]1)C)S(=O)(=O)NCCC1CCCN1C
InChI InChI=1S/C25H36N6O4S/c1-5-8-20-22-23(31(4)29-20)25(32)28-24(27-22)19-16-18(10-11-21(19)35-15-6-2)36(33,34)26-13-12-17-9-7-14-30(17)3/h10-11,16-17,26H,5-9,12-15H2,1-4H3,(H,27,28,32)
InChI Key IYFNEFQTYQPVOC-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/)
References
1. Ahn BO, Kang KK, Ahn GJ, Kwon JW, Kim WB, Kang KS, Lee YS. (2003)
Efficacy of DA-8159, a new PDE5 inhibitor, for inducing penile erection in rabbits with acute spinal cord injury.
Int J Impot Res, 15 (6): 405-11. [PMID:14671658]
2. Doh H, Shin CY, Son M, Ko JI, Yoo M, Kim SH, Kim WB. (2002)
Mechanism of erectogenic effect of the selective phosphodiesterase type 5 inhibitor, DA-8159.
Arch Pharm Res, 25 (6): 873-8. [PMID:12510841]
3. Oh TY, Kang KK, Ahn BO, Yoo M, Kim WB. (2000)
Erectogenic effect of the selective phosphodiesterase type 5 inhibitor, DA-8159.
Arch Pharm Res, 23 (5): 471-6. [PMID:11059826]
4. Shim HJ, Lee EJ, Kim SH, Kim SH, Yoo M, Kwon JW, Kim WB, Lee HS, Lee MG. (2000)
Pharmacokinetics, stability, and blood partition of DA-8159, a new phosphodiesterase V inhibitor.
Res Commun Mol Pathol Pharmacol, 108 (3-4): 275-86. [PMID:11913718]