plogosertib   Click here for help

GtoPdb Ligand ID: 12085

Synonyms: compound 384 [WO2009040556A1]
Compound class: Synthetic organic
Comment: We obtained the chemical structure for plogosertib from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a serine/threonine kinase inhibitor and antineoplastic. This Chemical structure mapped to PubChem CID 42640739, and compound 384 as claimed in patent WO2009040556A1 (Cyclacel Limited) which claims pyrimidine derivatives as inhibitors of kinases, 'particularly polo-like kinases' [1]. Plogosertib could be CYC140, Cyclacel's PLK1 clinical lead candidate. Cancer cells with mutated KRAS or p53(-) cells are sensitive to PLK1 inhibition. In these cells it induces prolonged mitotic arrest and apoptosis.
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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 10
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 106.17
Molecular weight 616.38
XLogP 3.27
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 COc1cc(ccc1Nc1ncc2c(n1)N(CC1(C(=O)N2C)CC1)C1CCCC1)C(=O)N[C@@H]1CC[C@H](CC1)N1CCN(CC1)C
Isomeric SMILES C1(CCCC1)N1c2c(N(C(=O)C3(C1)CC3)C)cnc(n2)Nc1c(cc(C(=O)N[C@@H]2CC[C@H](CC2)N2CCN(CC2)C)cc1)OC
InChI InChI=1S/C34H48N8O3/c1-39-16-18-41(19-17-39)25-11-9-24(10-12-25)36-31(43)23-8-13-27(29(20-23)45-3)37-33-35-21-28-30(38-33)42(26-6-4-5-7-26)22-34(14-15-34)32(44)40(28)2/h8,13,20-21,24-26H,4-7,9-12,14-19,22H2,1-3H3,(H,36,43)(H,35,37,38)/t24-,25-
InChI Key UFNLNMWVOMFWGS-SOAUALDESA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4-[(9-cyclopentyl-5-methyl-6-oxospiro[8H-pyrimido[4,5-b][1,4]diazepine-7,1'-cyclopropane]-2-yl)amino]-3-methoxy-N-[4-(4-methylpiperazin-1-yl)cyclohexyl]benzamide
International Nonproprietary Names Click here for help
INN number INN
12245 plogosertib
Synonyms Click here for help
compound 384 [WO2009040556A1]
Database Links Click here for help
CAS Registry No. 1137212-79-3 (source: WHO INN record)
GtoPdb PubChem SID 472319207
PubChem CID 42640739
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UniChem Compound Search for chemical match using the InChIKey UFNLNMWVOMFWGS-SOAUALDESA-N
UniChem Connectivity Search for chemical match using the InChIKey UFNLNMWVOMFWGS-SOAUALDESA-N