luminespib   Click here for help

GtoPdb Ligand ID: 9261

Synonyms: AUY922 | NVP-AUY922
PDB Ligand
Compound class: Synthetic organic
Comment: Luminespib (NVP-AUY922) is an intravenous HSP90 inhibitor with the potential to target a range of cancers. Discovered during a research collaboration with Novartis, Vernalis is now looking to partner the programme. We have drawn the structure as depicted in its INN record. Other chemistry resources show alternative tautomers. For example, PubChem CID 10096043 matches on CAS registry number, but is a structural tautomer.
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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 4
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 108.06
Molecular weight 465.23
XLogP 4.03
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 CCNC(=O)c1noc(c1c1ccc(cc1)CN1CCOCC1)c1cc(C(C)C)c(cc1O)O
Isomeric SMILES CCNC(=O)c1noc(c1c1ccc(cc1)CN1CCOCC1)c1cc(C(C)C)c(cc1O)O
InChI InChI=1S/C26H31N3O5/c1-4-27-26(32)24-23(18-7-5-17(6-8-18)15-29-9-11-33-12-10-29)25(34-28-24)20-13-19(16(2)3)21(30)14-22(20)31/h5-8,13-14,16,30-31H,4,9-12,15H2,1-3H3,(H,27,32)
InChI Key NDAZATDQFDPQBD-UHFFFAOYSA-N
References
1. Ernst JT, Liu M, Zuccola H, Neubert T, Beaumont K, Turnbull A, Kallel A, Vought B, Stamos D. (2014)
Correlation between chemotype-dependent binding conformations of HSP90α/β and isoform selectivity-Implications for the structure-based design of HSP90α/β selective inhibitors for treating neurodegenerative diseases.
Bioorg Med Chem Lett, 24 (1): 204-8. [PMID:24332488]
2. Huyan T, Li Q, Dong DD, Yang H, Zhang J, Huang QS, Yin DC, Shang P. (2016)
Heat shock protein 90 inhibitors induce functional inhibition of human natural killer cells in a dose-dependent manner.
Immunopharmacol Immunotoxicol, 38 (2): 77-86. [PMID:26642940]
3. Tao W, Chakraborty SN, Leng X, Ma H, Arlinghaus RB. (2015)
HSP90 inhibitor AUY922 induces cell death by disruption of the Bcr-Abl, Jak2 and HSP90 signaling network complex in leukemia cells.
Genes Cancer, 6 (1-2): 19-29. [PMID:25821558]