niraparib   Click here for help

GtoPdb Ligand ID: 8275

Synonyms: Akeega® (niraparib and abiraterone acetate) | compound 56 [PMID 19873981] | MK 4827 | MK-4827 | Zejula®
Approved drug PDB Ligand
niraparib is an approved drug (EMA & FDA (2017))
Compound class: Synthetic organic
Comment: Niraparib is a novel orally available poly(ADP-ribose) polymerase (PARP) inhibitor [4].
Click here for help

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.

✖

View interactive charts of activity data across species
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 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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 72.42
Molecular weight 320.16
XLogP 2.76
No. Lipinski's rules broken 0
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.

✖
Canonical SMILES NC(=O)c1cccc2c1nn(c2)c1ccc(cc1)C1CCCNC1
Isomeric SMILES NC(=O)c1cccc2c1nn(c2)c1ccc(cc1)[C@@H]1CCCNC1
InChI InChI=1S/C19H20N4O/c20-19(24)17-5-1-3-15-12-23(22-18(15)17)16-8-6-13(7-9-16)14-4-2-10-21-11-14/h1,3,5-9,12,14,21H,2,4,10-11H2,(H2,20,24)/t14-/m1/s1
InChI Key PCHKPVIQAHNQLW-CQSZACIVSA-N
References
1. Bryant HE, Schultz N, Thomas HD, Parker KM, Flower D, Lopez E, Kyle S, Meuth M, Curtin NJ, Helleday T. (2005)
Specific killing of BRCA2-deficient tumours with inhibitors of poly(ADP-ribose) polymerase.
Nature, 434 (7035): 913-7. [PMID:15829966]
2. Farmer H, McCabe N, Lord CJ, Tutt AN, Johnson DA, Richardson TB, Santarosa M, Dillon KJ, Hickson I, Knights C et al.. (2005)
Targeting the DNA repair defect in BRCA mutant cells as a therapeutic strategy.
Nature, 434 (7035): 917-21. [PMID:15829967]
3. Fong PC, Boss DS, Yap TA, Tutt A, Wu P, Mergui-Roelvink M, Mortimer P, Swaisland H, Lau A, O'Connor MJ et al.. (2009)
Inhibition of poly(ADP-ribose) polymerase in tumors from BRCA mutation carriers.
N Engl J Med, 361 (2): 123-34. [PMID:19553641]
4. Jones P, Altamura S, Boueres J, Ferrigno F, Fonsi M, Giomini C, Lamartina S, Monteagudo E, Ontoria JM, Orsale MV et al.. (2009)
Discovery of 2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (MK-4827): a novel oral poly(ADP-ribose)polymerase (PARP) inhibitor efficacious in BRCA-1 and -2 mutant tumors.
J Med Chem, 52 (22): 7170-85. [PMID:19873981]
5. Murai J, Huang SY, Das BB, Renaud A, Zhang Y, Doroshow JH, Ji J, Takeda S, Pommier Y. (2012)
Trapping of PARP1 and PARP2 by Clinical PARP Inhibitors.
Cancer Res, 72 (21): 5588-99. [PMID:23118055]
6. Reinbolt RE, Hays JL. (2013)
The Role of PARP Inhibitors in the Treatment of Gynecologic Malignancies.
Front Oncol, 3: 237. [PMID:24098868]