zaprinast   Click here for help

GtoPdb Ligand ID: 2919

Synonyms: M&B-22948
Compound class: Synthetic organic
Comment: Zaprinast is a phosphodiesterase inhibitor. It failed as a clinical drug candidate.
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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

zaprinast is commercially available from our sponsors

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 CDK toolkit. 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 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 96.55
Molecular weight 271.11
XLogP 3.54
No. Lipinski's rules broken 0
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.

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Canonical SMILES CCCOc1ccccc1c1nc(=O)c2c(n1)[nH][nH]n2
Isomeric SMILES CCCOc1ccccc1c1nc(=O)c2c(n1)[nH][nH]n2
InChI InChI=1S/C13H13N5O2/c1-2-7-20-9-6-4-3-5-8(9)11-14-12-10(13(19)15-11)16-18-17-12/h3-6H,2,7H2,1H3,(H2,14,15,16,17,18,19)
InChI Key REZGGXNDEMKIQB-UHFFFAOYSA-N
References
1. Davenport AP, Alexander SP, Sharman JL, Pawson AJ, Benson HE, Monaghan AE, Liew WC, Mpamhanga CP, Bonner TI, Neubig RR et al.. (2013)
International Union of Basic and Clinical Pharmacology. LXXXVIII. G protein-coupled receptor list: recommendations for new pairings with cognate ligands.
Pharmacol Rev, 65 (3): 967-86. [PMID:23686350]
2. Divorty N, Mackenzie AE, Nicklin SA, Milligan G. (2015)
G protein-coupled receptor 35: an emerging target in inflammatory and cardiovascular disease.
Front Pharmacol, 6: 41. [PMID:25805994]
3. Fisher DA, Smith JF, Pillar JS, St Denis SH, Cheng JB. (1998)
Isolation and characterization of PDE9A, a novel human cGMP-specific phosphodiesterase.
J Biol Chem, 273 (25): 15559-64. [PMID:9624146]
4. Kuc D, Zgrajka W, Parada-Turska J, Urbanik-Sypniewska T, Turski WA. (2008)
Micromolar concentration of kynurenic acid in rat small intestine.
Amino Acids, 35 (2): 503-5. [PMID:18235993]
5. Oka S, Ota R, Shima M, Yamashita A, Sugiura T. (2010)
GPR35 is a novel lysophosphatidic acid receptor.
Biochem Biophys Res Commun, 395 (2): 232-7. [PMID:20361937]
6. Southern C, Cook JM, Neetoo-Isseljee Z, Taylor DL, Kettleborough CA, Merritt A, Bassoni DL, Raab WJ, Quinn E, Wehrman TS et al.. (2013)
Screening β-Arrestin Recruitment for the Identification of Natural Ligands for Orphan G-Protein-Coupled Receptors.
J Biomol Screen, 18 (5): 599-609. [PMID:23396314]
7. Taniguchi Y, Tonai-Kachi H, Shinjo K. (2006)
Zaprinast, a well-known cyclic guanosine monophosphate-specific phosphodiesterase inhibitor, is an agonist for GPR35.
FEBS Lett, 580 (21): 5003-8. [PMID:16934253]
8. Tavoulari S, Schirris TJJ, Mavridou V, Thangaratnarajah C, King MS, Jones DTD, Ding S, Fearnley IM, Kunji ERS. (2022)
Key features of inhibitor binding to the human mitochondrial pyruvate carrier hetero-dimer.
Mol Metab, 60: 101469. [PMID:35278701]
9. Turko IV, Ballard SA, Francis SH, Corbin JD. (1999)
Inhibition of cyclic GMP-binding cyclic GMP-specific phosphodiesterase (Type 5) by sildenafil and related compounds.
Mol Pharmacol, 56 (1): 124-30. [PMID:10385692]
10. Zhao P, Sharir H, Kapur A, Cowan A, Geller EB, Adler MW, Seltzman HH, Reggio PH, Heynen-Genel S, Sauer M, Chung TD, Bai Y, Chen W, Caron MG, Barak LS, Abood ME. (2010)
Targeting of the orphan receptor GPR35 by pamoic acid: a potent activator of extracellular signal-regulated kinase and β-arrestin2 with antinociceptive activity.
Mol Pharmacol, 78 (4): 560-8. [PMID:20826425]