birinapant   Click here for help

GtoPdb Ligand ID: 7432

Synonyms: TL 32711 | TL-32711 | TL32711
PDB Ligand
Compound class: Synthetic organic
Comment: Birinapant is an experimental anti-cancer compound.
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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
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 12
Hydrogen bond donors 8
Rotatable bonds 19
Topological polar surface area 194.92
Molecular weight 806.43
XLogP 2.68
No. Lipinski's rules broken 3
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 CCC(C(=O)N1CC(CC1Cc1c([nH]c2c1ccc(c2)F)c1[nH]c2c(c1CC1CC(CN1C(=O)C(NC(=O)C(NC)C)CC)O)ccc(c2)F)O)NC(=O)C(NC)C
Isomeric SMILES CC[C@@H](C(=O)N1C[C@H](C[C@H]1Cc1c([nH]c2c1ccc(c2)F)c1[nH]c2c(c1C[C@@H]1C[C@@H](CN1C(=O)[C@@H](NC(=O)[C@@H](NC)C)CC)O)ccc(c2)F)O)NC(=O)[C@@H](NC)C
InChI InChI=1S/C42H56F2N8O6/c1-7-33(49-39(55)21(3)45-5)41(57)51-19-27(53)15-25(51)17-31-29-11-9-23(43)13-35(29)47-37(31)38-32(30-12-10-24(44)14-36(30)48-38)18-26-16-28(54)20-52(26)42(58)34(8-2)50-40(56)22(4)46-6/h9-14,21-22,25-28,33-34,45-48,53-54H,7-8,15-20H2,1-6H3,(H,49,55)(H,50,56)/t21-,22-,25-,26-,27-,28-,33-,34-/m0/s1
InChI Key PKWRMUKBEYJEIX-DXXQBUJASA-N
No information available.
Summary of Clinical Use Click here for help
Birinapant is being assessed in clinical trials to test effectiveness in patients with various types of cancer, either alone or in combination with other chemotherapeutic drugs. ClinicalTrials.com lists all currently registered trials using this compound.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Birinapant is a small molecule peptidomimetic of SMAC (second mitochondrial-derived activator of caspases) that selectively targets IAPs (inhibitors of apoptosis) and inhibits their activity. The compound effectively turns off NF-κB pro-survival signalling and synergises with pro-apoptotic ligands (eg TNFα and TRAIL) to direct cells towards the caspase-dependent pro-apoptotic pathway [1-4]. Birinapant exhibits somewhat selective binding activity for cellular inhibitor of apoptosis 1 (cIAP1) compared to cIAP2. Birinapant also antagonizes the function of XIAP (X-linked inhibitor of apoptosis) which permits activation of the caspases which terminate the extrinsic and intrinsic apoptosis pathways.