iniparib   Click here for help

GtoPdb Ligand ID: 8360

Synonyms: BSI-201 | SAR240550
PDB Ligand
Compound class: Synthetic organic
Comment: Iniparib was reported as PARP1 inhibitor [2] (or rather its metabolite 4-iodo-3-nitrosobenzamide was reported to inhibit PARP1 activity), however this action has been disputed [1,4].

iniparib 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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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 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 86.23
Molecular weight 291.93
XLogP 1.87
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 [O-][N+](=O)c1cc(ccc1I)C(=O)N
Isomeric SMILES [O-][N+](=O)c1cc(ccc1I)C(=O)N
InChI InChI=1S/C7H5IN2O3/c8-5-2-1-4(7(9)11)3-6(5)10(12)13/h1-3H,(H2,9,11)
InChI Key MDOJTZQKHMAPBK-UHFFFAOYSA-N
References
1. Liu X, Shi Y, Maag DX, Palma JP, Patterson MJ, Ellis PA, Surber BW, Ready DB, Soni NB, Ladror US et al.. (2012)
Iniparib nonselectively modifies cysteine-containing proteins in tumor cells and is not a bona fide PARP inhibitor.
Clin Cancer Res, 18 (2): 510-23. [PMID:22128301]
2. Mendeleyev J, Kirsten E, Hakam A, Buki KG, Kun E. (1995)
Potential chemotherapeutic activity of 4-iodo-3-nitrobenzamide. Metabolic reduction to the 3-nitroso derivative and induction of cell death in tumor cells in culture.
Biochem Pharmacol, 50 (5): 705-14. [PMID:7669074]
3. O'Shaughnessy J, Osborne C, Pippen JE, Yoffe M, Patt D, Rocha C, Koo IC, Sherman BM, Bradley C. (2011)
Iniparib plus chemotherapy in metastatic triple-negative breast cancer.
N Engl J Med, 364 (3): 205-14. [PMID:21208101]
4. Patel AG, De Lorenzo SB, Flatten KS, Poirier GG, Kaufmann SH. (2012)
Failure of iniparib to inhibit poly(ADP-Ribose) polymerase in vitro.
Clin Cancer Res, 18 (6): 1655-62. [PMID:22291137]