SGC-CBP30   Click here for help

GtoPdb Ligand ID: 7529

PDB Ligand Immunopharmacology Ligand Antimalarial Ligand
Compound class: Synthetic organic
Comment: CBP30 targets the CBP/p300 bromodomain, with much improved selectivity compared to the pan-BET bromodomain inhibitor (+)-JQ1 [3]. CBP30 has therapeutic potential against autoimmune diseases characterised by aberrant Th17 responses.
This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection.

The compound also has antimalarial activity. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
Click here for help

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.

✖

View interactive charts of activity data across species

SGC-CBP30 is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 65.55
Molecular weight 508.22
XLogP 5
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES COc1ccc(cc1Cl)CCc1nc2c(n1CC(N1CCOCC1)C)ccc(c2)c1c(C)noc1C
Isomeric SMILES COc1ccc(cc1Cl)CCc1nc2c(n1C[C@@H](N1CCOCC1)C)ccc(c2)c1c(C)noc1C
InChI InChI=1S/C28H33ClN4O3/c1-18(32-11-13-35-14-12-32)17-33-25-8-7-22(28-19(2)31-36-20(28)3)16-24(25)30-27(33)10-6-21-5-9-26(34-4)23(29)15-21/h5,7-9,15-16,18H,6,10-14,17H2,1-4H3/t18-/m0/s1
InChI Key GEPYBHCJBORHCE-SFHVURJKSA-N
Guide to Malaria Pharmacology Comments
Although SGC-CBP30 demonstrates low potency against P. falciparum, the compound is ~7-fold more selective for the parasite and could provide a starting point for the design of more potent analogues [1].

Potential Target/Mechanism Of Action: In silico docking studies predict that SGC-CBP30 participates in a typical hydrogen bond interaction with the conserved asparagine (Asn1436) of the P. falciparum histone acetyltransferase GCN5 (PfGCN5) bromodomain [1].