pimitespib   Click here for help

GtoPdb Ligand ID: 12284

Synonyms: compound 16e [PMID: 30525599] | Jeselhy® | TAS-116 | TAS116
Compound class: Synthetic organic
Comment: Pimitespib (TAS-116) is an orally bioavailable heat shock protein 90 α/β (HSP90α/β) inhibitor [6], that promotes proteasomal degradation of oncogenic HSP90 client proteins, and induces apoptosis of cells that overexpress (HSP90α/β). Reported to bind at the N-terminal ATP binding site of the target proteins [6]. Pimitespib was developed for potential antineoplastic activity [1,3-5].
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 6
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 108.4
Molecular weight 454.22
XLogP 3.87
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 CCc1cc(ccc1n1nc(c2c1nccc2n1cnc(c1)c1cnn(c1)C)C(C)C)C(=O)N
Isomeric SMILES CCc1c(ccc(c1)C(=O)N)n1c2nccc(c2c(n1)C(C)C)n1cc(nc1)c1cn(nc1)C
InChI InChI=1S/C25H26N8O/c1-5-16-10-17(24(26)34)6-7-20(16)33-25-22(23(30-33)15(2)3)21(8-9-27-25)32-13-19(28-14-32)18-11-29-31(4)12-18/h6-15H,5H2,1-4H3,(H2,26,34)
InChI Key NVVPMZUGELHVMH-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
3-ethyl-4-[4-[4-(1-methylpyrazol-4-yl)imidazol-1-yl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-1-yl]benzamide
International Nonproprietary Names Click here for help
INN number INN
11079 pimitespib
Synonyms Click here for help
compound 16e [PMID: 30525599] | Jeselhy® | TAS-116 | TAS116
Database Links Click here for help
BindingDB Ligand 126083
CAS Registry No. 1260533-36-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL3661115
DrugBank Ligand DB14876
GtoPdb PubChem SID 473153872
PubChem CID 67501411
Search Google for chemical match using the InChIKey NVVPMZUGELHVMH-UHFFFAOYSA-N
Search Google for chemicals with the same backbone NVVPMZUGELHVMH
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UniChem Compound Search for chemical match using the InChIKey NVVPMZUGELHVMH-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey NVVPMZUGELHVMH-UHFFFAOYSA-N